反应详情

Benzylchloroformate (15 ml) was added dropwise to a stirred suspension of 3-hydroxypiperidine hydrochloride (13.7 g) and triethylamine (30 ml) in dichloromethane (150 ml), maintaining the temperature below 15° C. throughout. Stirring was continued for three hours, then the solution was washed with water (4×100 ml) and saturated aqueous sodium chloride (100 ml), dried (PS paper) and concentrated. The residual oil was dissolved in ether (300 ml), washed with dilute hydrochloric acid (2×100 ml) and water (100 ml), dried (PS paper) and concentrated. The residue was purified by flash column chromatography, eluting first with hexane/ether (1:1) then ether to give 1-benzyloxycarbonylpiperidine-3-ol (7.1 g) as a colourless oil. NMR(d6DMSO): δ1.2-1.4(2H,m); 1.6-1.9(1H,m+1H,m); 2.8(1H,br s); 2.95(1H,m); 3.45(1H,m); 3.65(1H,br.d); 3.8(1H,dd); 4.85(1H,d); 5.1(2H,s); 7.3(5H,m); m/e 236(M+H)+.

1. temperaturemaintaining the temperature below 15° C. throughout
2. washthe solution was washed with water (4×100 ml) and saturated aqueous sodium chloride (100 ml)
3. customdried (PS paper)
4. concentrationconcentrated
5. dissolutionThe residual oil was dissolved in ether (300 ml)
6. washwashed with dilute hydrochloric acid (2×100 ml) and water (100 ml)
7. customdried (PS paper)
8. concentrationconcentrated
9. customThe residue was purified by flash column chromatography
10. washeluting first with hexane/ether (1:1)