Quinuclidine → 1-(3-Azido-3-methylbutyl)-1-azoniabicyclo[2.2.2]octane methanesulfonate

HRID 2061078Notes

Reaction equation

HRID 2061078 reaction equation
[CH3:1][S:2]([O:5][CH2:6][CH2:7][C:8]([N:11]=[N+:12]=[N-:13])([CH3:10])[CH3:9])(=[O:4])=[O:3].[N:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH2:16][CH2:15]2>CC(=O)CCC>[CH3:1][S:2]([O-:5])(=[O:4])=[O:3].[N:11]([C:8]([CH3:10])([CH3:9])[CH2:7][CH2:6][N+:14]12[CH2:21][CH2:20][CH:17]([CH2:18][CH2:19]1)[CH2:16][CH2:15]2)=[N+:12]=[N-:13]

Participants

4

Reactant 2

HCID 7527QuinuclidineHCID 105363033-Azido-3-methylbutyl methanesulfonate

Product 1

HCID 866427041-(3-Azido-3-methylbutyl)-1-azoniabicyclo[2.2.2]octane methanesulfonate

Reagents, catalysts & solvents 1

HCID 78952-PentanoneSolvent

Procedure

In a 1 dram vial, a solution of 3-azido-3-methylbutyl methanesulfonate (0.45 g, 2.19 mmol) and quinuclidine (0.21 g, 1.9 mmol) in 2-pentanone (2.0 mL) was heated on a heat block at 110° C. for 16 h. The suspension was cooled, filtered, and rinsed with diethyl ether (50 mL). The filtrate was discarded and the solid was dried under high vacuum to give a white solid. (052 g, 74.7%). 1H NMR (D2O, 400 MHz): δ 1.35 (s, 6H), 1.95-2.05 (m, 8H), 2.18-2.22 (pent, J=3.6, 1H), 2.82 (s, 3H), 3.24-3.30 (m, 2H), 3.38-3.45 (m, 6H). LRMS (ESI+) for C12H23N4+(223.2); Found: 223 (M+).

Workup

  1. temperatureThe suspension was cooled
  2. filtrationfiltered
  3. washrinsed with diethyl ether (50 mL)
  4. customthe solid was dried under high vacuum
  5. customto give a white solid

Sources & evidence

ORD record
ord-abc464f1af5e403da7b57be6807f7686
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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