2-(1,1-Dimethylethyl) 1-(phenylmethyl) (2S)-1,2-pyrrolidinedicarboxylate → L-Proline 1,1-dimethylethyl ester

HRID 1580895Notes

Reaction equation

HRID 1580895 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].[H][H]>CO.[Pd]>[NH:1]1[CH2:12][CH2:11][CH2:10][C@H:2]1[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4]

Participants

5

Reactant 2

HCID 70197992-(1,1-Dimethylethyl) 1-(phenylmethyl) (2S)-1,2-pyrrolidinedicarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 6453108L-Proline 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

9.15 g of Z-Pro-OtBu are hydrogenated in 100 ml of methanol and 1.0 g of Pd on charcoal (10 %) at room temperature. The hydrogen uptake has ended after 30 minutes. The solution is freed of catalyst by filtration and evaporated in a waterpump vacuum at 30°C. The resulting oil is homogeneous in a thin layer chromatogram on silica gel. Rf = 0.55 in the system chloroform-methanol (1:1).

Workup

  1. customat room temperature
  2. filtrationThe solution is freed of catalyst by filtration
  3. customevaporated in a waterpump vacuum at 30°C

Sources & evidence

ORD record
ord-f71f192fc7ed436cba8b1ee42c6b57d8
Source dataset
uspto-grants-1976_01
Patent number
US03934008

Reaction notes

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