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

HRID 2054521Notes

Reaction equation

HRID 2054521 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 2a (1.26 g, 66.7%), MS (CI) m/z 144.20 (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-a1c6ca014e74450d9133984ef490e43b
Source dataset
uspto-grants-2008_02
Patent number
US07329669B2

Reaction notes

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