Triethylamine → HCID 67497150, compound

HRID 1920549Notes

Reaction equation

Br.[Br-].[NH2:3][CH2:4][CH2:5][N+:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([O:14][C:15](=[O:30])[C:16]([OH:29])([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:7]2.C(N(CC)CC)C.[C:38]([Br:46])(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl>[Br-:46].[C:38]([NH:3][CH2:4][CH2:5][N+:6]12[CH2:13][CH2:12][CH:9]([CH2:10][CH2:11]1)[C@@H:8]([O:14][C:15](=[O:30])[C:16]([OH:29])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:7]2)(=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred suspension of (R)-1-(2-Amino-ethyl)-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide hydrobromide [50(H)] (0.28 g, 0.517 mmol) in DCM at 0° C. is added triethylamine (0.216 ml, 1.552 mmol) followed by benzoyl bromide (0.122 ml, 1.03 mmol). The reaction mixture is stirred at 0° C. for 1.5 hours and the solvent was removed in vacuo. Purification of the crude residue by chromatography on C18 silica, eluting with water:acetonitrile affords the title compound.

Workup

customthe solvent was removed in vacuo
customPurification of the crude residue by chromatography on C18 silica
washeluting with water

Sources & evidence

ORD record: ord-8c75ea5762234258862f27f96a56421e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168654B2

Reaction notes

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