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

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.