Benzene, 1-bromo-4-(trifluoromethyl)- → 8-methyl-3-(4-trifluoromethylphenyl)-8-azabicyclo[3.2.1]octan-3-ol

HRID 1870863Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.C([Li])CCC.[CH3:17][N:18]1[CH:23]2[CH2:24][CH2:25][CH:19]1[CH2:20][C:21](=[O:26])[CH2:22]2>>[CH3:17][N:18]1[CH:23]2[CH2:24][CH2:25][CH:19]1[CH2:20][C:21]([C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1)([OH:26])[CH2:22]2

Participants

Reactant 3

HCID 67872Benzene, 1-bromo-4-(trifluoromethyl)-

HCID 79038Npc164516

HCID 178418339Butyllithium

Product 1

HCID 4350948-methyl-3-(4-trifluoromethylphenyl)-8-azabicyclo[3.2.1]octan-3-ol

Procedure

The title compound was prepared from 4-bromobenzotrifluoride, n-butyllithium in hexanes (31.2 mL, 2.5M; 77.9 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-one (5 g, 36 mmol). Yield 6.2 g (60%) as a yellow solid, m.p. 189.2-190.5° C.

Sources & evidence

ORD record: ord-929f452864cf4b2e8dd3a31d4b43e485
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100275

Reaction notes

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