benzyl (2RS,3SR)-3-hydroxy-2,4,4-trimethylpyrrolidine-1-carboxylate → 2,4,4-Trimethylpyrrolidin-3-OL

HRID 906978Notes

Reaction equation

HRID 906978 reaction equation
[OH:1][CH:2]1[C:6]([CH3:8])([CH3:7])[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH:3]1[CH3:19]>CO.[C].[Pd]>[CH3:19][CH:3]1[CH:2]([OH:1])[C:6]([CH3:8])([CH3:7])[CH2:5][NH:4]1

Participants

4

Reactant 1

HCID 67390300benzyl (2RS,3SR)-3-hydroxy-2,4,4-trimethylpyrrolidine-1-carboxylate

Product 1

HCID 673891462,4,4-Trimethylpyrrolidin-3-OLYield 123.9%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension (20 mL) of benzyl (2RS,3SR)-3-hydroxy-2,4,4-trimethylpyrrolidine-1-carboxylate (842 mg) and 10% palladium carbon (50% water-containing, 110 mg) in methanol was stirred under a hydrogen atmosphere for 1.5 hr. The reaction mixture was filtered, oxalic acid (144 mg) was added to the filtrate, and the mixture was concentrated under reduced pressure to give the title compound as a colorless solid (yield: 512 mg, yield: 92%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionoxalic acid (144 mg) was added to the filtrate
  3. concentrationthe mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4daf305b659f411fa9683d67ad96b6d0
Source dataset
uspto-grants-2011_09
Patent number
US08013008B2

Reaction notes

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