Dimethylformamide → (1R,2R,5R)-8-Benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane

HRID 2088127Notes

Reaction equation

HRID 2088127 reaction equation
[C:1]1([C@:7]23[NH:14][C@H:11]([CH2:12][CH2:13]2)[CH2:10][CH2:9][C@H:8]3[O:15][Si:16]([CH2:21][CH3:22])([CH2:19][CH3:20])[CH2:17][CH3:18])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)C>[CH2:23]([N:14]1[C@@H:11]2[CH2:12][CH2:13][C@@:7]1([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C@H:8]([O:15][Si:16]([CH2:19][CH3:20])([CH2:21][CH3:22])[CH2:17][CH3:18])[CH2:9][CH2:10]2)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69685895(1R,2R,5R)-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane

Product 1

HCID 69889465(1R,2R,5R)-8-Benzyl-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octaneYield 83%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1R,2R,5R)-1-phenyl-2-triethylsilyloxy-8-azabicyclo[3.2.1]octane (Description 51; 100 mg, 0.315 mmol), benzyl bromide (0.5 ml), potassium carbonate (380 mg) and N,N-dimethylformamide (2 ml) was stirred at room temperature for 30 minutes. The reaction mixture was treated with diethyl ether, washed with water, brine, dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel to give the title compound (107 mg, 83%).

Workup

  1. washwashed with water, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-fbb1e2b53320403a9565f4a8552db4e2
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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