tert-butyl N-(2-oxocyclohexyl)carbamate → Tert-butyl 2-hydroxy-2-methylcyclohexylcarbamate

HRID 724261Notes

Reaction equation

HRID 724261 reaction equation
[CH3:1][Mg]Cl.[O:4]=[C:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]>O1CCCC1>[OH:4][C:5]1([CH3:1])[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[NH:11][C:12](=[O:18])[O:13][C:14]([CH3:15])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 5075026tert-butyl N-(2-oxocyclohexyl)carbamateHCID 178418332HCID 178418332, compound

Product 1

HCID 69571280Tert-butyl 2-hydroxy-2-methylcyclohexylcarbamateYield 21.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl magnesium chloride (3M in tetrahydrofuran, 19 ml, 57 mmol) was added to a solution of tert-butyl 2-oxocyclohexylcarbamate (4.0 g, 18.8 mmol) (Synth. Commun. (1992), 22(20), 3003–12) in tetrahydrofuran (80 ml) at −78° C. The mixture was allowed to warm to ambient temperature and was stirred for 3 h. The mixture was quenched by the addition of saturated ammonium chloride solution (20 ml) and was partitioned between water and diethyl diethyl ether. The organic phase was washed with water, brine, dried over MgSO4, and the solvent removed under reduced pressure to give a white solid which was purified by flash column chromatography using ethyl acetate:cyclohexane (98:2 to 70:30) as eluant to give the less polar diastereoisomer of tert-butyl 2-hydroxy-2-methylcyclohexylcarbamate (940 mg) as a white solid.

Workup

  1. customThe mixture was quenched by the addition of saturated ammonium chloride solution (20 ml)
  2. customwas partitioned between water and diethyl diethyl ether
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over MgSO4
  5. customthe solvent removed under reduced pressure
  6. customto give a white solid which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-a1c813dc5bf84cb0a1611647fb63e409
Source dataset
uspto-grants-2006_11
Patent number
US07141586B2

Reaction notes

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