1-Bromopent-2-yne → (R)-3-(2-Hydroxy-2,2-di-thiophen-2-yl-acetoxy)-1-pent-2-ynyl-1-azonia-bicyclo[2.2.2]octane bromide

HRID 1920554Notes

Reaction equation

[Br:1][CH2:2][C:3]#[C:4][CH2:5][CH3:6].[N:7]12[CH2:14][CH2:13][CH:10]([CH2:11][CH2:12]1)[C@@H:9]([O:15][C:16](=[O:29])[C:17]([OH:28])([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)[CH2:8]2>C(Cl)(Cl)Cl>[Br-:1].[OH:28][C:17]([C:18]1[S:19][CH:20]=[CH:21][CH:22]=1)([C:23]1[S:24][CH:25]=[CH:26][CH:27]=1)[C:16]([O:15][C@@H:9]1[CH:10]2[CH2:13][CH2:14][N+:7]([CH2:2][C:3]#[C:4][CH2:5][CH3:6])([CH2:12][CH2:11]2)[CH2:8]1)=[O:29]

Participants

Conditions

Temperature: 50 °C

Procedure

A solution of 1-bromo-2-pentyne (0.51 g, 3.44 mmol) in chloroform (2 ml) is treated with polymer supported TEA resin. After a few minutes this solution is added to a solution of hydroxy-di-thiophen-2-yl-acetic acid (R)-(1-aza-bicyclo-[2.2.2]oct-3-yl) ester (Example 70(ii)) (1.0 g, 2.87 mmol) in chloroform (2 ml). The resulting mixture is heated to 50° C. for 18 h and the mixture allowed to cool to room temperature. A white solid is isolated by filtration, washed with chloroform and dried. Recrystallisation from chloroform-acetonitrile, washing the resultant solid with cold acetonitrile, and drying under vacuum gives (R)-3-(2-Hydroxy-2,2-di-thiophen-2-yl-acetoxy)-1-pent-2-ynyl-1-azonia-bicyclo[2.2.2]octane bromide.

Workup

temperatureto cool to room temperature
customA white solid is isolated by filtration
washwashed with chloroform
customdried
customRecrystallisation from chloroform-acetonitrile
washwashing the resultant solid with cold acetonitrile
customdrying under vacuum

Sources & evidence

ORD record: ord-98009d84318443ad83673bcd97d264e9
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168654B2

Reaction notes

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