Aluminium lithium hydride → HCID 67773354, compound

Temperature

60 °C

To a solution of (S)-tert-butyl 1-(3-hydroxyazetidin-1-yl)-2,3-dimethyl-1-oxobutan-2-ylcarbamate (Compound X) (1.07 g, 3.74 mmol) in THF (50 mL) was a 1M solution of LAH in THF (16 ml, 16.00 mmol) dropwise added (over approximately 2 min) at −20° C. under a nitrogen atmosphere. The resultant mixture was stirred at rt for 30 min and heated at 60° C. over night. Additional LAH in THF (1M solution, 2 mL, 2 mmol) was added and the mixture was heated at 70° C. over night. The solvent was removed. 1,4-Dioxane (60 mL) and a 0.5M solution of LAH in ethylene glycol dimethyl ether (10 mL) was added to the residue. The resultant mixture was heated at 100° C. over night. The mixture was diluted with diethyl ether (150 mL) and the reaction was quenched with Na2SO4×10H2O. The mixture was filtered and the filtrate was concentrated under reduced pressure to give the title compound (0.8 g, quant.yield). The obtained crude product was used without further purification. LCMS (M+H)+: 187.

1. additiondropwise added (over approximately 2 min) at −20° C. under a nitrogen atmosphere
2. temperaturethe mixture was heated at 70° C. over night
3. customThe solvent was removed
4. addition1,4-Dioxane (60 mL) and a 0.5M solution of LAH in ethylene glycol dimethyl ether (10 mL) was added to the residue
5. temperatureThe resultant mixture was heated at 100° C. over night
6. additionThe mixture was diluted with diethyl ether (150 mL)
7. customthe reaction was quenched with Na2SO4×10H2O
8. filtrationThe mixture was filtered
9. concentrationthe filtrate was concentrated under reduced pressure

ORD record

ord-69c17feee1b9489dae932418b45043b1

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08361998B2