Chloral Hydrate → HCID 10944680, compound

Chloral hydrate (1.5 eq) was added to a solution of L-proline in CHCl3 (1 M), the suspension was refluxed (inverse Dean-Stark trap) for 6 h; the mixture was washed with water and the aq. phase re-extracted with CHCl3, the combined organic layers were dried and concentrated. Recrystallization (EtOH) of the residue afforded (3R,7aS)-3-(trichloromethyl)tetrahydro-1H-pyrrolo[1,2-c][1,3]oxazol-1-one in 72% yield. This material was dissolved in dry THF (0.12M), 2M LDA (1.5 eq) was added at −78° C. and the mixture was stirred for 40 min; 60% benzyl chloromethyl ether (3 eq) was added and stirring was continued from −78 to 0° C. for 3 h; after quenching with water the mixture was extracted with CHCl3 (3×), dried over Na2SO4 and concentrated. Flash chromatography (PE:EtOAc 5:1) afforded the title compound which was used without further characterisation in the next reaction (48%).

1. temperaturethe suspension was refluxed (inverse Dean-Stark trap) for 6 h
2. washthe mixture was washed with water
3. extractionthe aq. phase re-extracted with CHCl3
4. customthe combined organic layers were dried
5. concentrationconcentrated
6. customRecrystallization (EtOH) of the residue

ORD record

ord-cbc8f6d32b934d01aa5896b3203c5167

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08232390B2