(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid → (2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

HRID 469754Notes

Reaction equation

HRID 469754 reaction equation
CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.[C:14]([N:21]1[CH2:29][C@H:27]([OH:28])[CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CC(C)=O>[C:17]([O:16][C:14]([N:21]1[CH2:29][C:27](=[O:28])[CH2:26][C@H:22]1[C:23]([OH:25])=[O:24])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 88804(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acidHCID 131709961Jones' reagent

Product 1

HCID 11593804(2S)-1-(tert-butoxycarbonyl)-4-oxopyrrolidine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Jones' reagent (3.9 mL, 31.3 mmol) is added dropwise over a period of 5 mins to a solution of Boc-L-hydroxyproline (1 g, 4.3 mmol) in acetone (55 mL). The stirring is continued for an additional 30 minutes. The reaction is quenched with methanol (1 mL) and stirred at room temperature for 10 minutes. 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 130 [M+H+−100].

Workup

  1. customThe reaction is quenched with methanol (1 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-fcf48073551c4140b209427c86d7da72
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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