Ethyl Acetate → HCID 178468180, compound

HRID 1422930Notes

Reaction equation

HRID 1422930 reaction equation
C[Mg]Cl.[CH2:4]([O:11][C:12](=[O:26])[NH:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([C:20](=[O:25])N(OC)C)[CH2:16][CH2:15]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[C:27](OCC)(=O)C>O1CCCC1>[CH2:4]([O:11][C:12](=[O:26])[NH:13][C@H:14]1[CH2:15][CH2:16][C@H:17]([C:20](=[O:25])[CH3:27])[CH2:18][CH2:19]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 178418332HCID 178418332, compoundHCID 178502729HCID 178502729, compound

Product 1

HCID 178468180HCID 178468180, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-10 °C

Procedure

Methylmagnesium chloride (3M solution in tetrahydrofuran, 31 mg, 0.41 mmol, 2.2 eq) is added at −10° C. to a stirred solution of [trans-4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid benzyl ester (60 mg, 0.19 mmol, 1.0 eq) in tetrahydrofuran (5 mL). After 3 hours stirring at −10° C., solvent is evaporated and the residue is extracted with ethyl acetate (3×10 mL) and a saturated ammonium chloride aqueous solution (10 mL). The combined organic layers are dried over sodium sulfate, filtered and concentrated to give a residue that is purified by column chromatography (silica gel, eluent: petroleum ether:ethyl acetate, 2:1, v/v) to afford (trans-4-acetyl-cyclohexyl)-carbamic acid benzyl ester as a white solid (20 mg, 39% yield).

Workup

  1. customsolvent is evaporated
  2. extractionthe residue is extracted with ethyl acetate (3×10 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue that
  7. customis purified by column chromatography (silica gel, eluent

Sources & evidence

ORD record
ord-7048e2f7fe234e77a0f07020a1b05a1a
Source dataset
uspto-grants-2015_01
Patent number
US08927541B2

Reaction notes

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