tert-Butyl 3-aminopyrrolidine-1-carboxylate

Colorless low melting solid or liquid

Step (ii): Preparation of compound of formula (49)To a stirred solution of compound of formula (48) ( 1.1 5 grams, 4.16 mmol) in methanol ( 16.6 mL) was added 10 percent Pd/C (345 mg). Hydrogen pressure was applied through a double- layered balloon and the reaction was stirred for 16 hours. The reaction was filtered through a small pad of celite and the filtrate was removed under reduced pressure. The crude product was purified by silica gel flash column chromatography to obtain compound of formula (49) (640 mg). Yield: 82 percent.-NMR (CDCITriethylamine (0.75 mL, 5.34 mmol) and methanesulfonyl chloride (0.31 mL, 4.00 mmol) were added to a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol) in tetrahydrofuran (20 mL) at 0°C and stirred at the same temperature for 1.5 hours. Water and ethyl acetate were added to the reaction mixture, followed by extraction with ethyl acetate, and the extract solution was dried over anhydrous magnesium sulfate. The concentration residue was dissolved in N-methylpyrrolidinone (20 mL), followed by adding thereto sodium azide (520.8 mg, 8.01 mmol) at 0°C, and the resulting mixture was stirred with heating at 80°C for 3 hours. After the reaction mixture was cooled to 0°C, water and diethyl ether were added thereto, followed by two runs of extraction with diethyl ether, and the extract solution was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain an azide. To a solution of this azide in methanol (50 mL) was added palladium-carbon (250 mg) under a nitrogen atmosphere, and the resulting mixture was stirred for 3 hours under a hydrogen atmosphere. The reaction mixture was filtered by the use of Celite and the filtrate was distilled under reduced pressure to remove the solvent. The residue was purified by a silica gel chromatography to obtain tert-butyl 3-aminopyrrolidine-1-carboxylate (365.6 mg, 73percent).The starting materials were prepared as follows : 3RS-AMINO-PYRROLIDINE-1-CARBOXYLIC ACID TEFF-BUTYL ESTER To a solution of 3-aminopyrrolidine (0. 86 g, 10 MMOL) in CHCI3 (50 mi) at 0 C was added dropwise a solution of di-t-butyl dicarbonate ((BOC) 2O ; 2. 06 g, 10 MMOL) in CHCI3 (50 ML). The mixture stirred at room temperature for 1 hour, and then washed with brine, dried over K2CO3, filtered, and concentrated to give 1. 8 g of yellow oil in 98percent yield, which was used without further purification. 'H NMR : 8 3. 60-3. 28 (m, 4H), 3. 02 (m, 1 H), 2. 04 (m, 1 H), 1. 64 (m, 1 H), 1. 45 (s, 9H), 1. 45-1. 20 (m, 2H)Intermediate 138; 1 , 1 -dimethylethyl 3-amino-1 -pyrrolidinecarboxylate; 3-pyrrolidinamine (500 mg, 5.80 mmol), Tert-butyl phenyl carbonate (1.24 g, 6.38 mmol) was dissolved in DMF (5 ml) and stirred for 24 hours. Water and HCI 1 N was added until pH=3. The mixture was washed with dichloromethane (2 times). NaOH 1 N was added to the aqueous phase until pH=1 1-12 and was extracted with dichloromethane (4 times). The

Molecular Weight:186.25
XLogP3:0.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:2
Exact Mass:186.136827821
Monoisotopic Mass:186.136827821
Topological Polar Surface Area:55.6
Heavy Atom Count:13
Complexity:198
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes