4-Bromoanisole → 3-(4-methoxyphenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

HRID 1870862Notes

Reaction equation

HRID 1870862 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:15][N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][C:19](=[O:24])[CH2:20]2>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:19]2([OH:24])[CH2:20][CH:21]3[N:16]([CH3:15])[CH:17]([CH2:23][CH2:22]3)[CH2:18]2)=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 77304-BromoanisoleHCID 79038Npc164516HCID 178418339Butyllithium

Product 1

HCID 4344593-(4-methoxyphenyl)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared from 4-bromoanisole (15.1 g, 80.5 mmol), n-butyllithium in hexanes (31.2 mL, 2.5 M; 77.9 mmol) and 8-methyl-8-azabicyclo-[3.2.1]octan-3-one (5 g, 36 mmol) in anhydrous tetrahydrofuran (40 mL). Yield 2.1 g (24%), m.p. 161.8-162.3° C.

Sources & evidence

ORD record
ord-6b6ccf569ead46aa98f909101f242331
Source dataset
uspto-grants-2000_08
Patent number
US06100275

Reaction notes

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