Quinuclidinyl benzilate, (-)- → (R)-3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(2-methylamino-ethyl)-1-azonia-bicyclo [2.2.2]octane bromide hydrobromide

HRID 1920565Notes

Reaction equation

HRID 1920565 reaction equation
C(O[C:6](=O)[N:7]([CH2:9][CH2:10][Br:11])C)(C)(C)C.[N:13]12[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]1)[C@@H:15]([O:21][C:22](=[O:37])[C:23]([OH:36])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:14]2>CN(C=O)C>[BrH:11].[Br-:11].[OH:36][C:23]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:22]([O:21][C@@H:15]1[CH:16]2[CH2:17][CH2:18][N+:13]([CH2:10][CH2:9][NH:7][CH3:6])([CH2:20][CH2:19]2)[CH2:14]1)=[O:37]

Participants

4

Reactant 2

HCID 688566Quinuclidinyl benzilate, (-)-HCID 53743212HCID 53743212, compound

Product 1

HCID 67498057(R)-3-(2-Hydroxy-2,2-diphenyl-acetoxy)-1-(2-methylamino-ethyl)-1-azonia-bicyclo [2.2.2]octane bromide hydrobromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(2-Bromo-ethyl)-methyl-carbamic acid tert-butyl ester (0.09 g, 0.38 mmol) is added to a solution of hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (0.265 g, 0.79 mmol) in DMF (10 ml). The resulting mixture is heated at 60° C. for 5 hours and concentrated. This procedure is repeated twice giving the title compound as a mixture containing unreacted hydroxy-diphenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-c07ac422ef6046b9bef1567ea5c1c1b6
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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