2-Bromobenzyl alcohol → 8-Benzyl-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol

HRID 2265151Notes

Reaction equation

HRID 2265151 reaction equation
[O:1]=[C:2]1[CH2:8][CH:7]2[N:9]([C:10](OCC3C=CC=CC=3)=O)[CH:4]([CH2:5][CH2:6]2)[CH2:3]1.[C:20]1([Mg]Br)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O=[C:29]1[CH2:35][CH:34]2N(C(OC(C)(C)C)=O)[CH:31]([CH2:32][CH2:33]2)C1.[Li].BrC1C=CC=CC=1CO>>[CH2:10]([N:9]1[CH:4]2[CH2:5][CH2:6][CH:7]1[CH2:8][C:2]([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:29]=1)([OH:1])[CH2:3]2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 5

HCID 728502-Bromobenzyl alcoholHCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 3028194LithiumHCID 146825353-Oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylic acid benzyl esterHCID 178418255HCID 178418255, compound

Product 1

HCID 130912248-Benzyl-3-phenyl-8-azabicyclo[3.2.1]octan-3-ol

Procedure

2.80 g of the entitled compound was obtained as a white powder in the same manner as in Production Example 8-3, for which, however, benzyl 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylate and phenylmagnesium bromide were used in place of tert-butyl 3-oxo-8-aza-bicyclo[3.2.1]octane-8-carboxylate and the lithium reagent prepared from and 2-bromobenzyl alcohol and n-butyllithium-hexane solution used in Production Example 8-3.

Sources & evidence

ORD record
ord-f916fa7a41ed4e319eae749e6a9fe5c7
Source dataset
uspto-grants-2010_12
Patent number
US07855294B2

Reaction notes

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