Borane → Tert-butyl N-(1-cyclohexyl-2-hydroxyethyl)carbamate

HRID 1766051Notes

Reaction equation

HRID 1766051 reaction equation
[C:1]([O:5][C:6]([N:8](C1CCCCC1)CC(O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.[CH2:20]1[CH2:24][O:23][CH2:22][CH2:21]1>>[CH:20]1([CH:21]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:22][OH:23])[CH2:24][CH2:22][CH2:21][CH2:20][CH2:24]1

Participants

4

Reactant 3

HCID 6331BoraneHCID 8028TetrahydrofuranHCID 10563100n-Boc-n-cyclohexylglycine

Product 1

HCID 22037861Tert-butyl N-(1-cyclohexyl-2-hydroxyethyl)carbamateYield 66.7%

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 11a (1.26 g, 66.7%), MS (CI) m/z 144.2 (MH+-Boc).

Workup

  1. customThe reaction was quenched with MeOH (5 mL), volatiles
  2. customwere evaporated
  3. customthe residue was partitioned between water and EtOAc
  4. washThe organic layer was washed with saturated NaHCO3/water, brine
  5. dry with materialdried (sodium sulfate)
  6. customevaporated

Sources & evidence

ORD record
ord-0952fd117bc9451b9664416138e6573c
Source dataset
uspto-grants-2007_06
Patent number
US07229995B2

Reaction notes

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