(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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CAS No:
364077-84-9
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Formula:
C10H15NO5
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Chemical Name:
(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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Synonyms:
(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER;BOC-D-PRO(4-OXO);N-BOC-4-OXO-D-PROLINE;N-Boc-4-oxo-D-proline Methyl ester;1,2-Pyrrolidinedicarboxylic acid, 4-oxo-, 1-(1,1-diMethylethyl) ester, (2R)-;(R)-1-(tert-Butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid
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CAS No:
(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Basic Attributes
229.23
229.095016
2933990090
(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER Use and Manufacturing
Step 1 : Preparation of (R)-l-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid (29a) To a solution of (2R, 4R)-l-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid (14b) (51 g, 221 mmol) in dichloromethane (2023 mL) at 0 °C containing trichloroisocyanuric acid (51.3 g, 221 mmol) was added TEMPO (1.723 g, 11.03 mmol), stirred at 0 °C for 30 min and allowed to warm to room temperature overnight. The reaction mixture was diluted with water (100 mL) stirred for 30 min and concentrated in vacuum to remove dichloromethane. The reaction mixture was diluted with 200 mL ethyl acetate, filtered through a plug of Celite. The filtrate was acidified with 8 mL of 1 M HCI. The ethyl acetate layer was separated washed with water (4 x 200 mL), brine (100 mL), dried, filtered, and concentrated in vacuum to afford (R)-l-(tert-butoxycarbonyl)-4-oxopyrrolidine-2- carboxylic acid (29a) (38 g, 166 mmol, 75 percent yield) as a white solid; 1H MR (300 MHz, DMSO-i) δ 13.00 (s, 1H), 4.53 (m, 1H), 3.82 (dd, J = 18.6, 10.6 Hz, 1H), 3.66 (dd, J = 18.4, 4.4 Hz, 1H), 3.44 (s, 1H), 3.12 (m, 1H), 1.40 (s, 9H); MS (ES-) 228.2 (M-l), 457.3 (2M-1).
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(R)-4-OXO-PYRROLIDINE-1,2-DICARBOXYLIC ACID 1-TERT-BUTYL ESTER
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