Allyl bromide → (1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

HRID 2088177Notes

Reaction equation

HRID 2088177 reaction equation
[F:1][C:2]([F:37])([F:36])[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:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:17][C@H:18]3[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:44](Br)[CH:45]=[CH2:46]>CN(C)C=O.C(OCC)(=O)C>[CH2:46]([N:22]1[C@@H:19]2[C@H:18]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:17][C@@:16]1([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C@H:15]([O:14][CH2:13][C:5]1[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([C:2]([F:36])([F:1])[F:37])[CH:4]=1)[CH2:21][CH2:20]2)[CH:45]=[CH2:44]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 86586665(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Product 1

HCID 86586707(1R*,2R*,5S*,6R*)-8-Allyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1R*,2R*,5S*,6R*)-2-{[3,5-Bis(trifluoromethyl)phenyl]methoxy}-6-(tert-butoxycarbonyl)-1-phenyl-8-azabicyclo[3.2.1]octane (Example 25; 2.1 g, 4.0 mmol), potassium carbonate (1.7 g, 12.0 mmol) and allyl bromide (0.42 ml, 4.8 mmol) in dimethylformamide (10 ml) were stirred at room temperature for 5 hours. The mixture was diluted with ethyl acetate and washed with water. The organics were collected, dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography, eluting with 10% ethyl acetate/iso-hexane, (1.8 g, 80%).

Workup

  1. washwashed with water
  2. customThe organics were collected
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluting with 10% ethyl acetate/iso-hexane, (1.8 g, 80%)

Sources & evidence

ORD record
ord-bc20bcd6d5fa4e81aa855ef3cc407890
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

Loading…