Hydrogen Sulfide → 3-Hydroxy-3-mercaptomethylquinuclidine

Reaction equation

[CH2:1]=[C:2]1[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.[SH2:10].C[OH:12]>ClCCl>[OH:12][C:2]1([CH2:1][SH:10])[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1

Participants

Procedure

A solution of the epoxide of 3-methylene quinuclidine (100 g, 0.719 moles) in dichloromethane was cooled to a temperature between about 0 to 5° C. The solution was charged with methanol (100 ml). The mass was stirred for 10 to 15 minutes at this temperature range. To this cold solution hydrogen sulfide gas (50 g, 1.4 mol) was passed and after the passing was complete, the reaction was continued at this temperature for 2 to 3 hours, monitored by gas chromatography, whereupon the peak of epoxide of 3-methylene quinuclidine disappeared. After completion of the reaction, a dichloromethane solution of 3-hydroxy 3-mecapto methylquinuclidine in methanol was obtained. This solution was used for the next step.