Aluminium lithium hydride → tert-butyl N-(1-cyclohexyl-2-oxoethyl)carbamate

To an ice cooled solution of [cyclohexyl-(methoxy-methyl-carbamoyl)-methyl]-carbamic acid tert-butyl ester (12.3 g, 40 mmol) in THF (100 mL) was slowly added LAH (1M in THF; 45 mL), with the reaction mixture temperature maintained below 5° C. The ice bath was removed, and the reaction mixture was stirred at room temperature for 20 min. A solution of NaHSO4 (7.3 g) in water (10 mL) was then slowly added to the reaction mixture to quench the reaction. The reaction mixture was then filtered through Celite. EtOAc (300 mL) was added to the filtrate, and the organic layer washed with aqueous NaCl solution, dried with MgSO4 and evaporated to yield (1-cyclohexyl-2-oxo-ethyl)-carbamic acid tert-butyl ester as an oil, which was used in the next step without further purification.

1. temperaturewith the reaction mixture temperature maintained below 5° C
2. customThe ice bath was removed
3. additionA solution of NaHSO4 (7.3 g) in water (10 mL) was then slowly added to the reaction mixture
4. customto quench
5. customthe reaction
6. filtrationThe reaction mixture was then filtered through Celite
7. additionEtOAc (300 mL) was added to the filtrate
8. washthe organic layer washed with aqueous NaCl solution
9. dry with materialdried with MgSO4
10. customevaporated

ORD record

ord-ddac3f7c3e6c48aba3b1a1718b3c1729

Source dataset

uspto-grants-2009_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07531545B2