Water → (2R,4R)-tert-butyl 2-methyl-4-(tosyloxy)pyrrolidine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([OH:13])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:15]1([CH3:25])[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1.O>ClCCl.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:21]([C:18]2[CH:19]=[CH:20][C:15]([CH3:25])=[CH:16][CH:17]=2)(=[O:23])=[O:22])[CH2:10][C@H:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To a solution of 1.02 g of (2R,4R)-1-(t-butoxycarbonyl)-4-hydroxy-2-methylpyrrolidine (J. Med. Chem., 1988, 31, 1598-1611) in 10 ml of anhydrous dichloromethane, 1.7 ml of triethylamine and 1.16 g of p-toluenesulfonyl chloride were added, and then the mixture was stirred at room temperature overnight. The reaction solution was mixed with water, and followed by extraction with ethyl acetate twice. The organic layers were combined, washed in turn with water, 1N hydrochloric acid and a 1N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.54 g of the objective compound as a colorless oily product.
Workup
- extractionfollowed by extraction with ethyl acetate twice
- washwashed in turn with water, 1N hydrochloric acid
- dry with materiala 1N aqueous sodium hydroxide solution and dried over anhydrous sodium sulfate
- distillationthe solvent was distilled off under reduced pressure
- customThe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-7dea641aca3c49829f4b05f3cf36b2e6
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728131B2
Reaction notes
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