(+-)-3-Quinuclidinol → 3-(4-Methoxybenzylthio)quinuclidine

HRID 5112

Reaction equation

HRID 5112 reaction equation
CS(O[CH:6]1[CH:11]2[CH2:12][CH2:13][N:8]([CH2:9][CH2:10]2)[CH2:7]1)(=O)=O.N12CCC(CC1)C(O)C2.[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][SH:30])=[CH:27][CH:26]=1.[H-].[Na+]>>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][S:30][CH:6]2[CH:11]3[CH2:10][CH2:9][N:8]([CH2:13][CH2:12]3)[CH2:7]2)=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 15381(+-)-3-QuinuclidinolHCID 24758Sodium hydrideHCID 804074-Methoxy-alpha-toluenethiolHCID 4164941-Azabicyclo[2.2.2]oct-3-yl methanesulfonate

Product 1

HCID 197972653-(4-Methoxybenzylthio)quinuclidine

Procedure

The procedure described in Preparation 6-(2) was repeated, but using 3.7 g of 3-methanesulfonyloxyquinuclidine (prepared by the methanesulfonylation of 3-quinuclidinol), 3.0 ml of 4-methoxybenzyl mercaptan and 0.942 g of sodium hydride (as a 55% w/w suspension in mineral oil), to afford 1.74 g of the title compound as an oil.

Workup

  1. customThe procedure described in Preparation

Sources & evidence

ORD record
ord-b1ecc63b5cfd4eac90d16e7b577321a5
Source dataset
uspto-grants-1993_09
Patent number
US05242914

Linked notes

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