(R)-(+)-3-Chlorostyrene oxide → HCID 69817648, compound

HRID 2417416Notes

Reaction equation

HRID 2417416 reaction equation
[CH2:1]([NH:8][C@@H:9]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([C@@H:29]2[CH2:31][O:30]2)[CH:26]=[CH:27][CH:28]=1>C(O)C>[CH2:1]([N:8]([C@@H:9]([CH2:12][C:13]1[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=1)[CH2:10][OH:11])[CH2:31][C@@H:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[OH:30])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 69818787HCID 69818787, compound

Product 1

HCID 69817648HCID 69817648, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of (25)-2-(benzylamino)-3-(4-nitrophenyl)-1-propanol (6.0 g) in ethanol (60 ml) was added (2R)-2-(3-chlorophenyl)oxirane (4.86 g) and the mixture was refluxed for 23 hours. After cooling to room temperature, the solvent was removed by evaporation and the residue was chromatographed on silica gel (eluent: hexane/ethyl acetate=2/1) to give the (2S)-2-[N-benzyl-N-[(2R)-2-(3-chlorophenyl)-2-hydroxyethyl]amino]-3-(4-nitrophenyl)-1-propanol (5.46 g) as a yellow crystalline solid.

Workup

  1. temperaturethe mixture was refluxed for 23 hours
  2. customthe solvent was removed by evaporation
  3. customthe residue was chromatographed on silica gel (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-8b72acdc3f81443b88c0be490474912f
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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