反应详情

Said solution of (S)-azetidine-2-methanol was adjusted to pH 10 by adding 10% sulfuric acid, sodium hydrogen carbonate (2.00 g, 24.0 mmol) was then added and benzyloxycarbonyl chloride (ZCl) (4.00 g, 24.0mmol) was added at room temperature. Thereafter, stirring was continued for 14 hours. The mixture was adjusted to pH 7 and extracted with ethyl acetate (50 mL ×1), the extract was washed with water (50 mL×1) and dried over magnesium sulfate and, after filtering off the same, the filtrate was concentrated. This was subjected to column chromatography (Wakogel C-200) using toluene/ethyl acetate (1/1) as a mobile phase for separation and purification, whereby a pale yellow oil was obtained (1.50 g). Based on its proton NMR spectrum (FIG. 3), this was identified as the desired product (S)-N-benzyloxycarbonylazetidine-2-methanol (yield 69.1%). Further, as a byproduct, there was obtained (S)-2-N-benzyloxycarbonyl-1,4-butanediol (0.27 g, yield 11.4%). Its proton NMR spectrum is shown in FIG. 4.

1. additionwas then added
2. extractionextracted with ethyl acetate (50 mL ×1)
3. washthe extract was washed with water (50 mL×1)
4. dry with materialdried over magnesium sulfate
5. filtrationafter filtering off the same, the filtrate
6. concentrationwas concentrated
7. customfor separation and purification, whereby a pale yellow oil
8. customwas obtained (1.50 g)