m-Chloroperbenzoic acid → 1-[(4-Methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline

HRID 1764091Notes

Reaction equation

HRID 1764091 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][CH:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[CH2:11][CH2:10][N:9]2C)=[CH:5][CH:4]=1.ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[C:17]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[CH2:11][CH2:10][NH:9]2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 3562281-[(4-Methoxyphenyl)methyl]-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline

Product 1

HCID 938251-[(4-Methoxyphenyl)methyl]-1,2,3,4,5,6,7,8-octahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Alkyl allylic tertiary amines are dealkylated as illustrated by treatment of (-)-1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline in cold methylene chloride with m-chloroperbenzoic acid followed by the addition of aqueous ferrous chloride to provide a good yield of (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline with substantial if not complete retention of optical activity. The product is an intermediate in a synthesis of the analgesic known as butorphanol.

Sources & evidence

ORD record
ord-9707e6af0d1b4fbda29a1c1957941483
Source dataset
uspto-grants-1978_09
Patent number
US04115389

Reaction notes

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