ChemicalBook CAS DataBase List tert-Butyl 3-aminopyrrolidine-1-carboxylate

tert-Butyl 3-aminopyrrolidine-1-carboxylate synthesis

10synthesis methods

Product Name:tert-Butyl 3-aminopyrrolidine-1-carboxylate
CAS Number:186550-13-0
Molecular formula:C9H18N2O2
Molecular Weight:186.25

tert-butyl 3-(benzylamino)pyrrolidine-1-carboxylate

862906-31-8

186550-13-0

Step (ii): preparation of tert-butyl 3-aminopyrrolidine-1-carboxylate (Formula 49) To a stirred solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (Formula 48, 1.15 g, 4.16 mmol) in methanol (16.6 mL) was added 10% palladium/carbon catalyst (345 mg). The reaction mixture was stirred for 16 hours under a hydrogen atmosphere (hydrogen pressure applied via a double-layer balloon). Upon completion of the reaction, the mixture was filtered through a diatomaceous earth pad to remove the catalyst and the filtrate was concentrated under reduced pressure. The crude product was purified by silica gel fast column chromatography to afford the target compound tert-butyl 3-aminopyrrolidine-1-carboxylate (Formula 49, 640 mg) in 82% yield. 1H-NMR (CDCl3): δ 3.65-3.45 (m, 3H), 3.45-3.33 (m, 1H), 3.20-3.0 (m, 1H), 2.12-2.02 (m, 1H), 1.80-1.65 (m, 1H), 1.46 (s, 9H). Mass spectrum (m/z): 187 [M+H]+.

24424-99-5 Synthesis

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Yield:186550-13-0 98%

Reaction Conditions:

in chloroform at 20; for 1 h;

Steps:

A9 Example A9; 3RS- [4-AMINO-5- (2, 6-DIFLUORO-BENZOYL)-THIAZOL-2-YLAMINO]-PYRROLIDINE-1-CARBOXYLIC acid TERF-BUTYL ESTER
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 98% 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)

References:

PFIZER INC. WO2004/74283, 2004, A1 Location in patent:Page 38

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186550-13-0
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References