(R)-(+)-3-Chlorostyrene oxide → HCID 24822638, compound

HRID 1823072Notes

Reaction equation

HRID 1823072 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:18][C:19]1[CH:20]=[C:21]([C@@H:25]2[CH2:27][O:26]2)[CH:22]=[CH:23][CH:24]=1>C(O)C>[CH2:1]([N:8]([CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=1)[CH2:27][C@@H:25]([C:21]1[CH:22]=[CH:23][CH:24]=[C:19]([Cl:18])[CH:20]=1)[OH:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 22171438HCID 22171438, compound

Product 1

HCID 24822638HCID 24822638, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-benzyl-2-(4-bromophenyl)ethanamine (13.5 g) in ethanol (270 ml) was added (2R)-2-(3-chlorophenyl)oxirane (8.63 g) and the solution was refluxed for 48 hours. After cooling to room temperature, the solvent was removed by evaporation and the residue was chromatographed on silica gel (eluent:hexane/ethyl acetate=9/1) to give (1R)-2-[benzyl[2-(4-bromophenyl)ethyl]amino]-1-(3-chlorophenyl)ethanol (18.6 g) as a colorless oil.

Workup

  1. temperaturethe solution was refluxed for 48 hours
  2. customthe solvent was removed by evaporation
  3. customthe residue was chromatographed on silica gel (eluent:hexane/ethyl acetate=9/1)

Sources & evidence

ORD record
ord-0a301d943a604027842d6f7a8ff67a38
Source dataset
uspto-grants-2006_05
Patent number
US07037938B2

Reaction notes

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