Aluminium lithium hydride → HCID 86684769, compound

Temperature

0 °C

To a solution of [(R)-Cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid benzyl ester (27 g, 82 mmol) in THF (400 mL) at −20° C. was slowly added LiAlH4 (4.06 g, 106 mmol, 1.3 equiv). LiAlH4 was freshly ground from pellet purchased from Aldrich. During addition, the internal temperature was carefully monitored and did not rise above 0° C. After addition the mixture was stirred at 0° C. and the reaction was monitored by TLC and LCMS. After 1 hour, the reaction solution was cooled at −10° C. and quenched by slow addition of sat. aq. KHSO4 solution until pH=5. The mixture was partitioned between water and EtOAc. The phases were separated and the organic layer was concentrated. The residue was dissolved in EtOAc and the solution was washed with water, brine, dried over Na2SO4 and concentrated to give product ((R)-1-Cyclohexyl-2-oxo-ethyl)-carbamic acid benzyl ester 22 g (99%). The material was continued to next step with no further purification.

1. customat −20° C.
2. additionDuring addition
3. customdid not rise above 0° C
4. additionAfter addition the mixture
5. temperaturethe reaction solution was cooled at −10° C.
6. customquenched by slow addition of sat. aq. KHSO4 solution until pH=5
7. customThe mixture was partitioned between water and EtOAc
8. customThe phases were separated
9. concentrationthe organic layer was concentrated
10. dissolutionThe residue was dissolved in EtOAc
11. washthe solution was washed with water, brine
12. dry with materialdried over Na2SO4
13. concentrationconcentrated

ORD record

ord-ad54c1f563c247549f07b896c7a529f7

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040690B2