Sodium Bisulfate → HCID 53668323, compound

HRID 1801445Notes

Reaction equation

HRID 1801445 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])N(OC)C)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:21][Mg+].[Br-].OS([O-])(=O)=O.[Na+]>CCOCC>[C:1]([O:5][C:6](=[O:20])[NH:7][CH:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:19])[CH3:21])[CH2:12][CH2:13]1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 516919Sodium BisulfateHCID 24720928Tert-butyl trans-4-(N-methoxy-N-methylcarbamoyl)cyclohexylcarbamateHCID 178418689HCID 178418689, compound

Product 1

HCID 53668323HCID 53668323, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of [4-(methoxy-methyl-carbamoyl)-cyclohexyl]-carbamic acid tert-butyl ester (11 g, 38.4 mmol) in ether (200 mL), cooled to 0° C., was added MeMgBr (3M in ether, 32 mL, 96 mmol). The mixture was stirred 4 h at rt. 10% aq. NaHSO4 (200 mL) was carefully added. The two layers were decanted and the aq. layer was extracted with EA (100 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 2:1), affording the title methyl ketone as a white solid (7.4 g, 80% yield).

Workup

  1. customThe two layers were decanted
  2. extractionthe aq. layer was extracted with EA (100 mL)
  3. washlayers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by CC (Hept-EA 2:1)

Sources & evidence

ORD record
ord-235e370a302b43adb682281766e6bfad
Source dataset
uspto-grants-2013_01
Patent number
US08349829B2

Reaction notes

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