(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 469752Notes

Reaction equation

HRID 469752 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[CH3:14][C:15]([O:18][C:19]([N:21]1[C@H:25]([C:26]([O:28][CH3:29])=[O:27])[CH2:24][C@@H:23]([OH:30])[CH2:22]1)=[O:20])([CH3:17])[CH3:16]>CC(C)=O>[CH3:29][O:28][C:26]([C@@H:25]1[CH2:24][C:23](=[O:30])[CH2:22][N:21]1[C:19]([O:18][C:15]([CH3:17])([CH3:16])[CH3:14])=[O:20])=[O:27]

Participants

4

Reactant 2

HCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 131709961Jones' reagent

Product 1

HCID 109884851-tert-butyl 2-methyl (2S)-4-oxopyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (11 mL, 88.5 mmol) is added dropwise over a period of 5 minutes to a solution of Boc-HYP-OMe (3 g, 12.2 mmol) in acetone (150 mL). The stirring is continued for an additional 30 minutes. The reaction is quenched with methanol (3 mL) and stirred at room temperature overnight. The reaction mixture is filtered through Celite® and the filtrate is concentrated under reduced pressure. It was diluted with water and extracted with dichloromethane 3 times. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield the title compound. ESI m/z 144 [M+H+−100].

Workup

  1. customThe reaction is quenched with methanol (3 mL)
  2. filtrationThe reaction mixture is filtered through Celite®
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionIt was diluted with water
  5. extractionextracted with dichloromethane 3 times
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-598f62be16e744b994907738c8fd2293
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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