Water → (1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-8-(2-bromoacetyl)-1-phenyl-8-azabicyclo[3.2.1]octane
Reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[NH:22][C@@:16]2([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:17][CH2:18]3)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[Br:38][CH2:39][C:40](Br)=[O:41].O>C1COCC1>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:21][CH2:20][C@@H:19]3[N:22]([C:40](=[O:41])[CH2:39][Br:38])[C@@:16]2([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:17][CH2:18]3)[CH:4]=[C:3]([C:2]([F:29])([F:1])[F:30])[CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(1R*,2R*,5R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octane (Example 60; 162 mg, 0.38 mmol) was dissolved in THF (3 ml) and triethylamine (0.059 ml, 0.42 mmol) added. The reaction mixture was cooled to 0° C. then bromoacetyl bromide (0.037 ml, 0.42 mmol) added, then the mixture warmed to room temperature. A further 1.1 equivalents of triethylamine (0.059 ml), and bromoacetyl bromide (0.037 ml) were added and the reaction mixture stirred at room temperature for 15 minutes. The reaction mixture was poured into water, extracted with ethyl acetate (×3), dried (MgSO4), and concentrated in vacuo to give the title compound.
Workup
- temperaturethe mixture warmed to room temperature
- extractionextracted with ethyl acetate (×3)
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-37d85fa153584b428cd7f35887b94f4f
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06727249B2
Reaction notes
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