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

HRID 28500Notes

Reaction equation

HRID 28500 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 4a (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-2e5d3a502d464a9f913b30a437bfa2a0
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Reaction notes

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