2-Bromobenzyl alcohol → Benzyl 4-(2-chlorophenyl)-4-hydroxypiperidine-1-carboxylate

HRID 2265148Notes

Reaction equation

HRID 2265148 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:4][CH2:3]1.[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Mg]Br.BrC1C=CC=CC=1CO.C([Li])CCC>>[Cl:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:2]1([OH:1])[CH2:3][CH2:4][N:5]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])[CH2:6][CH2:7]1

Participants

5

Reactant 4

HCID 728502-Bromobenzyl alcoholHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 178418339ButyllithiumHCID 178478041HCID 178478041, compound

Product 1

HCID 23157061Benzyl 4-(2-chlorophenyl)-4-hydroxypiperidine-1-carboxylate

Procedure

9.74 g of the entitled compound was obtained as a pale yellow oily substance in the same manner as in Production Example 8-3, for which, however, benzyl 4-oxopiperidine-1-carboxylate was used in place of tert-butyl 3-oxo-8-aza-bicyclo-[3.2.1]octane-8-carboxylate used in Production Example 8-3, and 2-chlorophenylmagnesium bromide was used in place of the lithium reagent prepared from 2-bromobenzyl alcohol and n-butyllithium.

Sources & evidence

ORD record
ord-1950dbe6c9334b188344b4d0d6084a4f
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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