Diethyl Ether → (+/-)-benzyl (1S,2S)-2-hydroxy-2-methylcyclohexylcarbamate

HRID 1408955Notes

Reaction equation

HRID 1408955 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH:3]1[NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[Mg+].[Br-].[CH3:22]COCC>C1COCC1>[OH:1][C@@:2]1([CH3:22])[CH2:7][CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:8][C:9](=[O:18])[O:10][CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14219048Benzyl (2-oxocyclohexyl)carbamateHCID 178418689HCID 178418689, compound

Product 1

HCID 86707706(+/-)-benzyl (1S,2S)-2-hydroxy-2-methylcyclohexylcarbamateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl 2-oxocyclohexylcarbamate (173 mg, 0.7 mmol) in THF (3 mL) was cooled to −78° C. and added MeMgBr in ether (0.7 mL, 2.1 mmol) dropwise via syringe. The ice bath was removed and the reaction was allowed to stir at rt for 3 h. The reaction was quenched with sat. aqueous NH4Cl (1 mL) and partitioned between ethyl acetate and water. The layers were separated and the organic layer washed with brine, dried (Na2SO4), filtered and concentrated. The product was subjected to flash chromatography on silica gel (10% to 70% ethyl acetate/hexanes) to afford the title compound (81 mg, 88% yield) as a single diastereomer. This material was used as is in the next transformation.

Workup

  1. customThe ice bath was removed
  2. customThe reaction was quenched with sat. aqueous NH4Cl (1 mL)
  3. custompartitioned between ethyl acetate and water
  4. customThe layers were separated
  5. washthe organic layer washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-2765bb223ed54ee18e0c1cfffa1e0a65
Source dataset
uspto-grants-2014_12
Patent number
US08921368B2

Reaction notes

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