2-Bromoethyl methyl ether → 4-[Hydroxy(diphenyl)methyl]-1-[2-(methyloxy)ethyl]-1-azoniabicyclo[2.2.1]heptane bromide

HRID 499662Notes

Reaction equation

HRID 499662 reaction equation
[N:1]12[CH2:7][C:4]([C:8]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[OH:9])([CH2:5][CH2:6]1)[CH2:3][CH2:2]2.[Br:22][CH2:23][CH2:24][O:25][CH3:26]>CC#N>[Br-:22].[OH:9][C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]12[CH2:7][N+:1]([CH2:23][CH2:24][O:25][CH3:26])([CH2:6][CH2:5]1)[CH2:2][CH2:3]2

Participants

4

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 426258561-Azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol

Product 1

HCID 160414004-[Hydroxy(diphenyl)methyl]-1-[2-(methyloxy)ethyl]-1-azoniabicyclo[2.2.1]heptane bromideYield 24.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Following the general procedure outlined in Example 1, 1-azabicyclo[2.2.1]hept-4-yl(diphenyl)methanol (30.8 mg, 0.110 mmol) and 1-bromo-2-(methyloxy)ethane (0.03 mL, 0.3 mmol) in 2 CH3CN/3 CHCl3 (2.5 nm) were reacted to give the desired product (11.1 mg, 24%). EI-MS m/z 338 (M+) Rt (1.64 min).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-99ad66f05e594a69b9f89b8b68737205
Source dataset
uspto-grants-2010_08
Patent number
US07767691B2

Reaction notes

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