Diethyl Ether → (R)-1-[(3-Fluoro-phenylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2192315Notes

Reaction equation

HRID 2192315 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[S:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:11])[CH2:2]2.[Br:24][CH2:25][C:26]([NH:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[CH:30]=1)=[O:27].C(OCC)C.CCCC(C)C>C(#N)C>[Br-:24].[F:35][C:31]1[CH:30]=[C:29]([NH:28][C:26]([CH2:25][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10]([C:12]2([C:19]4[S:20][CH:21]=[CH:22][CH:23]=4)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:2]3)=[O:27])[CH:34]=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 78922-MethylpentaneHCID 34164032-bromo-N-(3-fluorophenyl)acetamideHCID 58348375HCID 58348375, compound

Product 1

HCID 86655273(R)-1-[(3-Fluoro-phenylcarbamoyl)-methyl]-3-(1-thiophen-2-yl-cycloheptanecarbonyloxy)-1-azonia-bicyclo[2.2.2]octane bromideYield 55.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-Thiophen-2-yl-cycloheptanecarboxylic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Example 5d) (96 mg) and 2-bromo-N-(3-fluoro-phenyl)-acetamide (Example 8a) (67 mg) were dissolved in acetonitrile (2 mL) and left overnight. Diethyl ether (10 mL) and isohexane (8 mL) were added and the mixture was left overnight. The resulting crystals were filtered off and washed with diethyl ether to afford the titled compound (90 mg).

Workup

  1. waitthe mixture was left overnight
  2. filtrationThe resulting crystals were filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-479bf25aeb0444b48ae82b3c66877e74
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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