tert-butyl N-(3-bromopropyl)carbamate → (R)-1-(3-tert-Butoxycarbonylamino-propyl)-3-(2-hydroxy-2,2-di-thiophen-2-yl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 1920553Notes

Reaction equation

HRID 1920553 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:23])[C:11]([OH:22])([C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[CH2:2]2.[C:24]([NH:31][CH2:32][CH2:33][CH2:34][Br:35])([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]>CN(C=O)C>[Br-:35].[C:27]([O:26][C:24]([NH:31][CH2:32][CH2:33][CH2:34][N+:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:23])[C:11]([OH:22])([C:12]1[S:13][CH:14]=[CH:15][CH:16]=1)[C:17]1[S:18][CH:19]=[CH:20][CH:21]=1)[CH2:2]2)=[O:25])([CH3:30])([CH3:29])[CH3:28]

Participants

4

Reactant 2

HCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 44232927(R)-Quinuclidin-3-yl 2-hydroxy-2,2-di(thiophen-2-yl)acetate

Product 1

HCID 67497707(R)-1-(3-tert-Butoxycarbonylamino-propyl)-3-(2-hydroxy-2,2-di-thiophen-2-yl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Hydroxy-di-thiophen-2-yl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl) ester (0.758 g, 2.17 mmol) and 3(BOC-amino) propylbromide (0.775 g, 3.25 mmol) are dissolved in DMF (7 ml) and heated at 60° C. for 2.5 hours. The solvent is removed in vacuo and purification of the crude residue by chromatography on C18 silica, eluting with water:acetonitrile affords the titled compound as an oil.

Workup

  1. customThe solvent is removed in vacuo and purification of the crude residue by chromatography on C18 silica
  2. washeluting with water

Sources & evidence

ORD record
ord-d2e5c8920b1347d9bcb9f2f9e25c1d15
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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