(+-)-3-Quinuclidinol → 1-azabicyclo[2.2.2]octan-3-yl N-(4-bromophenyl)carbamate

HRID 609633Notes

Reaction equation

HRID 609633 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([OH:9])[CH2:2]2.[Br:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([O:9][C:18](=[O:19])[NH:17][C:14]1[CH:15]=[CH:16][C:11]([Br:10])=[CH:12][CH:13]=1)[CH2:2]2

Participants

3

Reactant 2

HCID 15381(+-)-3-QuinuclidinolHCID 756094-Bromophenyl isocyanate

Product 1

HCID 100191861-azabicyclo[2.2.2]octan-3-yl N-(4-bromophenyl)carbamateYield 60%

Procedure

3-Quinuclidinol and 4-bromophenyl isocyanate were used. Filtration of the precipitated solid from the cooled reaction mixture afforded the title compound (60%) as a white solid: mp 217.5-219.5° C.; FAB LRMS m /z (relative intensity, %)328(16), 327 ([MH+ with Br81 ], 100), 326(16), 325 ([MH+ with Br79 ], 100).

Workup

  1. filtrationFiltration of the precipitated solid
  2. customfrom the cooled reaction mixture

Sources & evidence

ORD record
ord-8db0203a650d49ee8e10395f06ef2745
Source dataset
uspto-grants-1999_12
Patent number
US05998429

Reaction notes

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