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(R)-(+)-1-Boc-3-aminopyrrolidine structure
(R)-(+)-1-Boc-3-aminopyrrolidine structure

(R)-(+)-1-Boc-3-aminopyrrolidine

Iupac Name:tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate
CAS No.: 147081-49-0
Molecular Weight:186.25
Modify Date.: 2022-11-25 01:09
Introduction:

A mixture of (R) -tert-butyl 3-azidopyrrolidine-1-carboxylate (250 mg, 1.18 mmol) and Pd/C (10, 50 mg) in methanol (10 mL) was stirred at rt under HThe compound (R) -3- azido-pyrrolidine-1-carboxylate (250mg, 1.18mmol) and Pd / C (10percent, 50mg) wasdissolved in methanol (10mL of), at room temperature, normal pressure hydrogen reduction, the reaction isstopped after 12h the reaction, filtration, and the filtrate was concentrated to give 210mg of colorless liquid: (R) -3- Amino-pyrrolidine-1-carboxylate, yield: 96percent.To a solution of product 178 (907 mg, 4.27 mmol, 1.0 eq.) in 25 mL of methanol, palladium on charcoal (454 mg, 0.43 mmol, 0.1 eq.) is added. The reaction medium is submitted to hydrogenation at atmospheric pressure and at room temperature for 6 hours. The reaction medium is then filtered on celite and concentrated under dry conditions under reduced pressure. The expected compound is obtained as a yellow oil (740 mg, 93percent).Step 5-1: Production of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine; To 5.56 g of (S)-1-(tert-butoxycarbonyl)-3-(methanesulfonyloxy)pyrrolidine produced by the method described in Production was added 36.4 g of a 28percent by weight aqueous ammonia solution, and the mixture was stirred at 90°C for 19 hrs (internal pressure: about 4 barr). After cooling, ammonia was removed by distillation, and thereto were added 10 ml of water and 3.21 g of a 30percent by weight aqueous sodium hydroxide solution. After the aqueous solution was concentrated under reduced pressure, 10 ml of a saturated brine was added thereto, and the target substance was extracted with 20 ml of ethyl acetate three times. Thus obtained organic layer was washed with 3 ml of a saturated brine, followed by concentration under reduced pressure to give the title compound as 3.20 g of a yellow liquid (chemical purity: 63.5 areapercent, , optical purity: 100percent e.e., yield: 64percent). It was ascertained that 41.4percent of the optically active 1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine represented by the above formula (3) was contaminated with respect to the HPLC area value of the title compound, while 7.8percent of 1-(tert-butoxycarbonyl)-3, 4-dehydropyrrolidine represented by the above formula (4) was contaminated with respect to the HPLC area value of the title compound.; Step 6-1: Production of (R)-1-(tert-butoxycarbonyl)-3-aminopyrrolidine; To 11.2 g of a solution in toluene including 7.83 g of (S)-1-(tert-butoxycarbonyl)-3-(methanesulfonyloxy)pyrrolidine produced by the method described in Production was added 62.7 g of a 40percent by weight aqueous ammonia solution, and the mixture was stirred at 80°C for 10 hrs (internal pressure: about 8 barr). After cooling, the reaction mixture was concentrated under reduced pressure, to which 31.3 g of a saturated brine, 19.6 g of toluene, and 4.13 g of a 30percent by weight aqueous sodium hydroxide solution were added. Thus obtained organic layer was concentrated under reduced pressure to give the title compound as 5.09 g of a yellow liquid (chemical purity: 74.5 areapercent, yield: 74percent, optical purity: 99.4percent ee). It was ascertained that 18.1percent of the optically active 1-(tert-butoxycarbonyl)-3-hydroxypyrrolidine represented by the above formula (3) was contaminated with respect to the HPLC area value of the title compound, while 4.1percent of 1-(tert-butoxycarbonyl)-3, 4-dehydropyrrolidine represented by the above formula (4) was contaminated with respect to the HPLC area value of the title compound.

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1. Names and Identifiers
1.1 Name
(R)-(+)-1-Boc-3-aminopyrrolidine
1.2 Synonyms

(3R)-(+)-1-(tert-Butoxycarbonyl)-3-aminopyrrolidine (3R)-(+)-1-Boc-3-aminopyrrolidine (3R)-(+)-3-Amino-1-(tert-butoxycarbonyl)pyrrolidine (3R)-(+)-3-Amino-1-Boc-pyrrolidine (3R)-3-amino-1-(tert-butoxycarbonyl)pyrrolidine (3R)-3-Amino-1-pyrrolidinecarboxylic acid 1,1-dimethylethyl ester (3R)-3-Aminopyrrolidine, N1-BOC protected (3R)-3-Aminopyrrolidine-1-carboxylic Acid T-butyl Ester (R)-(+)-N-BOC-3-AMINOPYRROLIDINE (R)-(+)-N-tert-Butoxycarbonyl-3-aminopyrroli (R)-1-Boc-3-Aminopyrrolidine (R)-3-Amino-1-Boc-pyrroli... (R)-3-AMINO-1-BOC-PYRROLIDINE (R)-3-AMINO-1-N-BOC-PYRROLIDINE (R)-3-amino-N-(t-butoxycarbonyl)-pyrrolidine (R)-3-AMINO-N-BOC-PYRROLIDINE (R)-TERT-BUTYL 3-AMINOPYRROLIDINE-1-CARBOXYLATE 1-Boc-3-(R )-aminopyrrolidine 1-Boc-3-(R)-aminopyrrolidine 1-PYRROLIDINECARBOXYLIC ACID, 3-AMINO-, 1,1-DIMETHYLETHYL ESTER, (3R) 1-Pyrrolidinecarboxylic acid, 3-amino-, 1,1-dimethylethyl ester, (3R)- 2-Methyl-2-propanyl (3R)-3-amino-1-pyrrolidinecarboxylate 3-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID TERT-BUTYL ESTER, (R) MFCD03419272 R-(+)-1-Boc-3-aminopyrrolidine R-1-N-BOC-3-AMINO PYRROLIDINE T5NTJ AVOX1&1&1 CZ &&R Form Tert-butyl (3R)-3-aminopyrrolidine-1-carboxylate tert-butyl (R)-3-amino-pyrrolidine-1-carboxylate tert-Butyl-(3R)-3-aminopyrrolidin-1-carboxylat

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1.3 CAS No.
147081-49-0
1.4 CID
854070
1.5 EINECS(EC#)
604-556-0
1.6 Molecular Formula
C9H18N2O2 (isomer)
1.7 Inchi
InChI=1S/C9H18N2O2/c1-9(2,3)13-8(12)11-5-4-7(10)6-11/h7H,4-6,10H2,1-3H3/t7-/m1/s1
1.8 InChIkey
CMIBWIAICVBURI-SSDOTTSWSA-N
1.9 Canonical Smiles
CC(C)(C)OC(=O)N1CCC(C1)N
1.10 Isomers Smiles
CC(C)(C)OC(=O)N1CC[C@H](C1)N
2. Properties
2.1 Density
1.098
2.1 Melting point
243-244°C
2.1 Boiling point
243-244℃
2.1 Refractive index
1.4720
2.1 Flash Point
196?
2.1 Precise Quality
186.13700
2.1 PSA
55.56000
2.1 logP
1.59270
2.1 Appearance
colorless to light yellow liquid
2.2 Storage
Keep Cold. Air Sensitive.
2.3 Chemical Properties
Colorless to light yellow liqui (R)-(+)-1-Boc-3-aminopyrrolidine Preparation Products And Raw materials Raw materials
2.4 Color/Form
Pale-yellow to Yellow-brown Liquid
2.5 pKa
9.55±0.20(Predicted)
2.6 StorageTemp
Keep in dark place,Inert atmosphere,2-8°C
3. Safety and Handling
3.1 Symbol
GHS05, GHS06
3.1 Hazard Codes
C; Xn
3.1 Signal Word
Danger
3.1 Risk Statements
R22
3.1 Safety Statements
26-36/37/39
3.1 Packing Group
3.1 Hazard Class
8
3.1 Hazard Declaration
H301-H318
3.1 RIDADR
UN 2810 6.1/PG 3
3.1 Caution Statement
P280-P301 + P310-P305 + P351 + P338
3.1 WGK Germany
3
3.1 Safety

Hazard Codes:?CorrosiveC,HarmfulXn
Risk Statements: 22-41-44
R22: (R)-(+)-1-Boc-3-aminopyrrolidine (CAS NO.147081-49-0) is harmful if swallowed.?
R41: Risk of serious damage to the eyes.?
R44: Risk of explosion if heated under confinement.
Safety Statements: 26-36/37/39
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2810 6.1/PG 3

3.2 Sensitive
Air Sensitive
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 3

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H301 Toxic if swallowed

H318 Causes serious eye damage

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P310 Immediately call a POISON CENTER/doctor/\u2026

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Uses
(R)-(+)-1-Boc-3-aminopyrrolidine may be used to prepare:
  • Descarboxamide analog and Na-methylated analogs of 4-N-(Nω-nitro-L-argininyl)-trans-4-amino-L-proline amide.
  • Histamine 3 (H3) receptor antagonists containing pyrrolidin-3-yl-N-methylbenzamide moiety.
7.1 Chemical Properties
Colorless to light yellow liqui
8. Computational chemical data
  • Molecular Weight: 186.25g/mol
  • Molecular Formula: C9H18N2O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: 0.4
  • Exact Mass: 186.136827821
  • Monoisotopic Mass: 186.136827821
  • Complexity: 198
  • Rotatable Bond Count: 2
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 3
  • Topological Polar Surface Area: 55.6
  • Heavy Atom Count: 13
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceBzMAAAAAAAAAAAAAAAAAAAAWAAAAAAAAAAAAAAAAAAAAAAHgAQAAAADGzBgAQCCANABAAIAAAAGAAAAAAAAAAAAIAIAAAAQAAAwAAcAAAAFgCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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