Ethanol → L-Proline 1,1-dimethylethyl ester

HRID 1757712Notes

Reaction equation

HRID 1757712 reaction equation
[C:1]([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1CC(=O)[C@H](CC1C=CC=CC=1)NC(OCC1C=CC=CC=1)=O)([CH3:4])([CH3:3])[CH3:2].C(O)C.CO.[BH4-].[Na+]>C(O)(C)C>[C:1]([O:5][C:6](=[O:34])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 4311764Sodium borohydrideHCID 70041054N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert.butyl ester

Product 1

HCID 6453108L-Proline 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2 g (4.3 mmol) of N-[[N-(benzyloxycarbonyl)-L-phenylalanyl]methyl]-L-proline tert.butyl ester (prepared as described in Example 1) were dissolved in 25 ml of isopropanol, 25 ml of ethanol and 25 ml of methanol and the solution was stirred at room temperature for 4 hours in the presence of 0.4 g (10.7 mmol) of sodium borohydride. The solvent was removed by evaporation and the residue was partitioned between 50 ml of ethyl acetate and 25 ml of water. The organic phase was washed with saturated sodium chloride solution and dried over anhydrous sodium sulphate. The solvent was removedby evaporation and there were obtained 2 g of N-[3(S)-(benzyloxyformamido)-2(R and S)-hydroxy-4-phenylbutyl]-L-proline tert.butyl ester as a clear gum: Rf (System C): 0.68 and 0.57.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between 50 ml of ethyl acetate and 25 ml of water
  3. washThe organic phase was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporation

Sources & evidence

ORD record
ord-c08d897de1d24122b416ab7836e37b21
Source dataset
uspto-grants-1995_08
Patent number
US05446161

Reaction notes

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