Imidazole → (1S)-2-amino-1-phenylethan-1-ol

HRID 1682740Notes

Reaction equation

HRID 1682740 reaction equation
[Si](Cl)(C(C)(C)C)(C)C.[C:9](OCC)(=O)[C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11].[NH:22]1C=CN=C1>CN(C)C=O>[NH2:22][CH2:9][C@H:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 6951557ethyl mandelate, (S)-

Product 1

HCID 643217(1S)-2-amino-1-phenylethan-1-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
40 °C

Procedure

A solution of 31.4 g of t-butyldimethylsilyl chloride in 200 ml of dimethylformamide was added dropwise to a solution of 25 g of ethyl (S)-(+)-mandelate and 28.4 g of imidazole in 800 ml of dimethylformamide, and the resulting mixture was stirred overnight at 40° C. At the end of this time, the dimethylformamide solvent was removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 10:1 by volume mixture of hexane and ethyl acetate as the eluent, to give the title compound having an Rf=0.84 (thin layer chromatography over silica gel, using a 10: 1by volume mixture of hexane and ethyl acetate as the developing solvent).

Workup

  1. customAt the end of this time, the dimethylformamide solvent was removed by distillation under reduced pressure
  2. customthe resulting residue was purified by column chromatography through silica gel
  3. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-ccf29251f1404a559cfb40773064aa77
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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