1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester → HCID 86655293, compound

HRID 2192375Notes

Reaction equation

HRID 2192375 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:25][CH2:26][C:27]([NH:29][C:30]1[O:31][CH:32]=[CH:33][N:34]=1)=[O:28]>CC#N>[Br-:25].[O:31]1[CH:32]=[CH:33][N:34]=[C:30]1[NH:29][C:27]([CH2:26][N+:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10]([C:12]1([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2)=[O:28]

Participants

4

Reactant 2

HCID 591796191-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)esterHCID 67027754HCID 67027754, compound

Product 1

HCID 86655293HCID 86655293, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Phenyl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 14e) (0.31 mmol) and 2-bromo-N-oxazol-2-yl-acetamide (Example 48a) (0.31 mmol) were stirred in anhydrous MeCN at room temperature for 18 hours. The reaction mixture was concentrated in vacuo and the yellow solid purified by flash silica gel column chromatography eluting with 0-15% MeOH/dichloromethane to give the title compound (100 mg) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe yellow solid purified by flash silica gel column chromatography
  3. washeluting with 0-15% MeOH/dichloromethane

Sources & evidence

ORD record
ord-169870043c9243cf961579574520ed68
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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