Aluminium lithium hydride → HCID 67772010, compound

Temperature

45 °C

To a solution of methyl 1-cyclopentyl-2-(3-hydroxyazetidin-1-yl)-2-oxoethylcarbamate (Compound K2.1) (1.89 g, 7.37 mmol) in THF (50 mL) was a 1M solution of LAH in THF (30 mL, 30.0 mmol) dropwise added (over approximately 5 min) at rt under a nitrogen atmosphere. The resultant mixture was stirred at rt for 30 min and heated at 45° C. over night. Additional LAH in THF (1M solution, 10 mL) was added and the mixture was heated at 65° C. for 1 day. The mixture was diluted with Et2O (150 mL) and the reaction was quenched with Na2SO4×10H2O. The mixture was filtered and a HCl solution in EtOH was added (1.25N, 15 mL) to the filtrate. The filtrate was concentrated under reduced pressure and the residue was co-evaporated with MeOH to give the title compound (1.5 g, 75.0%). The obtained crude product was used without further purification. LCMS (M+H)+: 199.

1. additiondropwise added (over approximately 5 min) at rt under a nitrogen atmosphere
2. temperaturethe mixture was heated at 65° C. for 1 day
3. customthe reaction was quenched with Na2SO4×10H2O
4. filtrationThe mixture was filtered
5. additiona HCl solution in EtOH was added (1.25N, 15 mL) to the filtrate
6. concentrationThe filtrate was concentrated under reduced pressure

ORD record

ord-e4269f3e9f5f4c66a3618b3f99046cd5

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2