(R)-(+)-3-Chlorostyrene oxide → HCID 54012491, compound

HRID 2299697Notes

Reaction equation

HRID 2299697 reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)[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]([CH2:31][C@@H:29]([C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([Cl:22])[CH:24]=1)[OH:30])[CH:9]1[CH2:15][CH2:14][CH2:13][C:12]2[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:11]=2[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10898919(R)-(+)-3-Chlorostyrene oxideHCID 18007303HCID 18007303, compound

Product 1

HCID 54012491HCID 54012491, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of N-benzyl-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amine (0.30 g) and (R)-3-chlorophenyl oxirane (0.18 g) in ethanol (0.6 ml) was refluxed overnight. The reaction mixture was evaporated in vacuo, and the residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1). The product (0.43 g) was treated with 4N hydrogen chloride in ethyl acetate and powdered from diisopropyl ether to afford (1R)-2-[N-benzyl-N-(3-methoxy-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)amino]-1-(3-chlorophenyl)ethanol (0.40 g).

Workup

  1. temperaturewas refluxed overnight
  2. customThe reaction mixture was evaporated in vacuo
  3. customthe residue was purified by column chromatography on silica gel eluting with a mixture of hexane and ethyl acetate (5:1)
  4. additionThe product (0.43 g) was treated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-7f4d2e6c83a24d8d9412567fc6a1834e
Source dataset
uspto-grants-2002_12
Patent number
US06495546B1

Reaction notes

Loading…