3-Hydroxyazetidine hydrochloride → HCID 86708505, compound

A mixture of oxetan-3-one (0.5 g, 6.94 mmol), azetidin-3-ol hydrochloride (1.140 g, 10.41 mmol) and 4 A molecular sieves (1.5 g) in dichloromethane (10 mL) was stirred at room temperature for 4 h. Sodium triacetoxyborohydride (2.94 g, 13.88 mmol) was added and the reaction mixture was stirred at room temperature overnight. The precipitate was filtered through a pad of celite and the filtrate was diluted with ethyl acetate (more precipitate appeared) and filtered again. The filtrate was concentrated in vacuo and the crude product was purified by flash chromatography on silica gel using an automated ISCO system (80 g column, eluting with 3-10% 2N ammonia in methanol/dichloromethane). 1-(oxetan-3-yl)azetidin-3-ol was obtained as colorless oil.

1. stirringthe reaction mixture was stirred at room temperature overnight
2. filtrationThe precipitate was filtered through a pad of celite
3. additionthe filtrate was diluted with ethyl acetate (
4. filtrationfiltered again
5. concentrationThe filtrate was concentrated in vacuo
6. customthe crude product was purified by flash chromatography on silica gel using
7. washan automated ISCO system (80 g column, eluting with 3-10% 2N ammonia in methanol/dichloromethane)

ORD record

ord-43f4b08c5a0149f99af063e7861ee964

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09273057B2