Acetone → L-Proline, 1-(1-methylethyl)- (9CI)

HRID 547262Notes

Reaction equation

HRID 547262 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7].[CH3:9][C:10]([CH3:12])=O>CO.[Pd]>[CH:10]([N:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[C:6]([OH:8])=[O:7])([CH3:12])[CH3:9]

Participants

5

Reactant 2

HCID 180AcetoneHCID 145742L-Proline

Product 1

HCID 45084886L-Proline, 1-(1-methylethyl)- (9CI)Yield 101.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of (S)-pyrrolidine-2-carboxylic acid (5 g, 50 mmol), acetone (5.52 mL, 50 mmol) and 10% Pd/C (2.5 g) in methanol (100 mL) was stirred under hydrogen atmosphere for 6 to 12 hours. The reaction mixture was filtered on a pad of celite and the filtrate was concentrated. The residue obtained was filtered through a column of silica gel to afford (S)-1-isopropylpyrrolidine-2-carboxylic acid (8.0 g, 94%) as a colorless solid.

Workup

  1. filtrationThe reaction mixture was filtered on a pad of celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue obtained
  4. filtrationwas filtered through a column of silica gel

Sources & evidence

ORD record
ord-c7bcac0a3a7c493a88ae0a1727cc1612
Source dataset
uspto-grants-2011_05
Patent number
US07939513B2

Reaction notes

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