(S)-3-AMINO-1-CBZ-PYRROLIDINE synthesis
- Product Name:(S)-3-AMINO-1-CBZ-PYRROLIDINE
- CAS Number:122536-72-5
- Molecular formula:C12H16N2O2
- Molecular Weight:220.27
122536-74-7
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122536-72-5
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Yield: 100%
Reaction Conditions:
with hydrogenchloride in 1,4-dioxane;dichloromethane at 20; for 2 h;
Steps:
14
(3S)-3-amino-pyrrolidine-1-carboxylic acid, benzyl ester. To a solution of (3-S)-3-tert-butoxcarbonylamino-pyrrolidine-1-carboxylic acid, benzyl ester (8 g, 25 mmol) in dichloromethane (50 mL) was added a saturated solution of hydrogen chloride in dioxane (50 mL) at room temperature. After 2 h, the solvent was evaporated and the crude reaction mixture was diluted with dichloromethane (300 mL) followed by treatment with aquous sodium bicarbonate (200 mL), brine (50 mL) and dried (Na2SO4). The solvent was evaporated to give benzyl ester (3S)-3-amino-pyrrolidine-1-carboxylic acid, benzyl ester in quantitative yield. 1H NMR (300 MHz, CDCl3): in δ 7.35-7.25 (m, 5 H), 5.11 (s, 2 H), 3.68-3.44 (m, 5 H), 3.18-3.10 (m, 1 H), 2.05-2.03 (m, 1 H), 1.80-1.69 (m, 1H); MS (ESI+), 221 (M+H); Rf=0.88.
References:
Chaturvedula, Prasad V.;Luo, Guanglin;Vig, Shikha;Poindexter, Graham S.;Beno, Brett R, US2004/224901, 2004, A1 Location in patent:Page/Page column 11
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100858-33-1
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122536-72-5
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