(2S)-1-((tert-butoxy)carbonyl)azetidine-2-carboxylic acid → tert-butyl (2S)-2-(hydroxymethyl)azetidine-1-carboxylate

(S)-1-(tert-butoxycarbonyl)-2-azetidinecarboxylic acid (10.42 g, 49.4 mmol) was introduced into a 500-mL pear-shaped flask, and tetrahydrofuran (200 mL) was added to dissolve the compound. Then, a tetrahydrofuran solution of 10 M borane-dimethyl sulfide complex salt (9.87 mL, 98.7 mmol) was slowly added at 0° C., and the mixture was heated to reflux for 2 hours while stirring. The reaction solution was left to cool, and then was concentrated under reduced pressure. Ice water (100 mL) was poured thereto, and the mixture was extracted with ethyl acetate (200 mL×2). The extract was washed with saturated brine (200 mL), and then dried over anhydrous sodium sulfate. After filtering the extract, the filtrate was concentrated under reduced pressure to obtain the title compound (8.03 g, 42.9 mmol, 87%) as an oily matter.

1. dissolutionto dissolve the compound
2. temperaturethe mixture was heated
3. temperatureto reflux for 2 hours
4. waitThe reaction solution was left
5. temperatureto cool
6. concentrationwas concentrated under reduced pressure
7. additionIce water (100 mL) was poured
8. extractionthe mixture was extracted with ethyl acetate (200 mL×2)
9. washThe extract was washed with saturated brine (200 mL)
10. dry with materialdried over anhydrous sodium sulfate
11. filtrationAfter filtering the extract
12. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-f91273e92a4f4dcda87058ae6bdff673

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08129366B2