Dimethylformamide → HCID 20722845, compound

HRID 2088129Notes

Reaction equation

HRID 2088129 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:15][CH2:14][C@H:13]2[NH:16][C@:10]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:23](Br)[CH:24]=[CH2:25].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>C(OCC)C>[Si:1]([O:8][C@H:9]1[CH2:15][CH2:14][C@H:13]2[N:16]([CH2:25][CH:24]=[CH2:23])[C@:10]1([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:11][CH2:12]2)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 69890521HCID 69890521, compound

Product 1

HCID 20722845HCID 20722845, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (1S,2S,5S)-2-(tert-butyldimethylsilyloxy)-1-phenyl-8-azabicyclo[3.2.1]octane (Description 55; 237 mg), allyl bromide (0.4 ml), potassium carbonate (230 mg) and N,N-dimethylformamide (2 ml) was stirred at room temperature for 2 hours. The reaction mixture was treated with diethyl ether, washed with water and brine, then dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-25%) to give the title compound (230 mg, 98% two steps).

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 0-25%)

Sources & evidence

ORD record
ord-fc284f67f20142d0bdf6028a36dc9fdb
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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