Potassium Carbonate → cis-4-(tert-Butoxycarbonylamino)cyclohexanol

HRID 931480Notes

Reaction equation

HRID 931480 reaction equation
C([O:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7][CH2:6]1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][CH:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:7][CH2:6]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23062736HCID 23062736, compound

Product 1

HCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanolYield 107.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-[[(tert-butoxy)carbonyl]amino]cyclohexyl acetate (2.43 g, 9.44 mmol, 1.00 equiv), methanol (30 mL) and potassium carbonate (2 g, 14.37 mmol, 1.50 equiv) was stirred overnight at 25° C. The resulting mixture was concentrated under vacuum. Water (50 mL) was added and the resulting solution was extracted with 3×70 mL of dichloromethane. The organic layers were combined and washed with 2×200 mL of brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum to give 2.19 g of crude tert-butyl N-(4-hydroxycyclohexyl)carbamate as yellow oil.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. additionWater (50 mL) was added
  3. extractionthe resulting solution was extracted with 3×70 mL of dichloromethane
  4. washwashed with 2×200 mL of brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-de1ba60dc0d1486cb844642bf44fd80a
Source dataset
uspto-grants-2016_03
Patent number
US09296732B2

Reaction notes

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