反应详情

To a vigourosly stirred solution of 4-hydroxypiperidine-1-carboxylic acid tert-butyl ester (2.07 g, 10.3 mmol) in DMF (25 mL) was added a 60% sodium hydride dispersion in mineral oil (500 mg, 12.5 mmol). After stirring for 20 min, methyl iodide (0.9 mL, 14.5 mmol) was added and the resulting mixture stirred for 48 h before being added to a mixture of water and brine (250 mL, 1:1). Extraction with ethyl acetate (4×50 mL), washing of the combined extracts with brine (100 mL) and drying (MgSO4) gave, after concentration, a residue which was purified via flash chromatography (silica gel, ethyl acetate/hexane, 1:1) to give the title compound as a colourless oil. δH (CDCl3): 1.50 (9H, s), 1.52, 1.88 (4H, 2m) 3.12 (2H, ddd), 3.18 (1H, m), 3.19 (3H, s), 3.77 (2H, m); Rf0.33 (ethyl acetate/hexane: 1/1).

1. stirringthe resulting mixture stirred for 48 h
2. extractionExtraction with ethyl acetate (4×50 mL)
3. washwashing of the combined extracts with brine (100 mL)
4. dry with materialdrying (MgSO4)
5. customgave
6. concentrationafter concentration
7. customa residue which was purified via flash chromatography (silica gel, ethyl acetate/hexane, 1:1)