Reaction #56778

Reaction equation

N-(t-butyloxycarbonyl)cyclohexylglycine

THF

Borane

→

tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate

Yield 66.7%

Conditions

Workup

1. 1
   OtherThe reaction was quenched with MeOH (5 mL), volatiles
2. 2
   Otherwere evaporated
3. 3
   Otherthe residue was partitioned between water and EtOAc
4. 4
   WashThe organic layer was washed with saturated NaHCO3/water, brine
5. 5
   Dryingdried (sodium sulfate)
6. 6
   Otherevaporated

Procedure

A solution of N-(t-butyloxycarbonyl)cyclohexylglycine (2.0 g, 7.77 mmol) in anhydrous THF (10 mL) was cooled to 0° C. Borane solution (1 M in THF, 15.5 mL, 15.5 mmol) was added slowly and the reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with MeOH (5 mL), volatiles were evaporated and the residue was partitioned between water and EtOAc. The organic layer was washed with saturated NaHCO3/water, brine, dried (sodium sulfate), and evaporated to give tert-butyl 1-cyclohexyl-2-hydroxyethylcarbamate 4a (1.26 g, 66.7%), MS (CI) m/z 144.2 (MH+-Boc).

Source