Borane → HCID 22127280, compound

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH:13]=2)=[CH:4][CH:3]=1.B.[O:16]1CCCC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH:13]2[OH:16])=[CH:4][CH:3]=1

Participants

Reactant 3

HCID 6331Borane

HCID 8028Tetrahydrofuran

HCID 787451-Methyl-4-(4-chlorophenyl)-1,2,3,6-tetrahydropyridine

Product 1

HCID 22127280HCID 22127280, compound

Procedure

In an analogous manner to that described in Example 1(c), from 4-(4-chloro-phenyl)-1-methyl-1,2,3,6-tetrahydropyridine [U.S. Pat. No. 3,320,265] by hydroboration using borane in tetrahydrofuran there was obtained (3RS,4RS)-4-(4-chloro-phenyl)-1-methyl-piperidin-3-ol which, after recrystallization from a mixture of methylene chloride and hexane, formed colourless crystals of m.p.: 99-100° C.

Sources & evidence

ORD record: ord-4d4fca3affb64b6aa79d445238529c62
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150526

Reaction notes

Loading…