Aluminium lithium hydride → HCID 67772010, Verbindung

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-Eintrag

ord-e4269f3e9f5f4c66a3618b3f99046cd5

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08361998B2