(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester → 1-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

HRID 490125Notes

Reaction equation

HRID 490125 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>C(Cl)(Cl)Cl>[O:1]=[C:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8])[C@H:4]([C:14]([O:16][CH3:17])=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 178418287HCID 178418287, compound2×

Product 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylateYield 132.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

150 g of 1-tert-butyl 2-methyl(2S,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate, 264 g of pyridinium chlorochromate, and 75 g of celite were stirred in 2 L of chloroform at room temperature. During this stirring, another 100 g of pyridinium chlorochromate was added, and the reaction mixture was stirred for a total of 7 days. The reaction solution was filtered through celite (washed with 500 mL of chloroform), and the filtrate was concentrated under reduced pressure to obtain 197 g of black oil. The residue thus obtained was purified by column chromatography (silica gel 60, mobile phase: ethyl acetate/n-hexane=2/1; v/v) to obtain 119 g of the titled compound (yellow oily substance).

Workup

  1. filtrationThe reaction solution was filtered through celite (washed with 500 mL of chloroform)
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c1b9b4cce1f24942a441f3085e1994b5
Source dataset
uspto-grants-2009_05
Patent number
US07528124B2

Reaction notes

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