Ethyl Acetate → Benzyl (3-hydroxycyclohexyl)carbamate

HRID 1013812Notes

Reaction equation

HRID 1013812 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([NH2:8])[CH2:3]1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>O>[CH2:25]([O:24][C:22](=[O:23])[NH:8][CH:4]1[CH2:5][CH2:6][CH2:7][CH:2]([OH:1])[CH2:3]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 112404593-Aminocyclohexanol

Product 1

HCID 14476840Benzyl (3-hydroxycyclohexyl)carbamateYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Treat a mixture of 3-hydroxycyclohexyl amine (10 g, 86.96 mmol), potassium carbonate (18 g, 130 mmol), ethyl acetate (150 mL) and water (70 mL) with benzyl chloroformate (22.17 g, 130 mmol). Stir the reaction at room temperature for 12 hours. Separate the organic layer, dry the organic over sodium sulfate, filter and concentrate. Add diethyl ether to the residuer. Filter the resulting white precipitate and air dry to afford 19.1 g of the title compound (88%). MS (m/z): 250 (M+).

Workup

  1. additionTreat
  2. customthe reaction at room temperature for 12 hours
  3. customSeparate the organic layer
  4. dry with materialdry the organic over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate
  7. filtrationFilter the resulting white precipitate and air
  8. customdry

Sources & evidence

ORD record
ord-804318bcbfbb46449e650c709fde728c
Source dataset
uspto-grants-2011_07
Patent number
US07981918B2

Reaction notes

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