Ethanol → L-Proline 1,1-dimethylethyl ester

HRID 54056Notes

Reaction equation

HRID 54056 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 removed by 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. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-6ea51b55ca0c44bd892858b539c184aa
Source dataset
uspto-grants-1997_04
Patent number
US05620987

Reaction notes

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