Hydrochloric Acid → 4-Amino-4-phenylcyclohexan-1-one

HRID 1893325Notes

Reaction equation

HRID 1893325 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:9]1[C:13]2([CH2:18][CH2:17][C:16](=[N:19]S(C(C)(C)C)=O)[CH2:15][CH2:14]2)OCC1.Cl>C1COCC1>[NH2:9][C:13]1([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:14][CH2:15][C:16](=[O:19])[CH2:17][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 59733754N-(1,4-dioxaspiro[4.5]dec-8-ylidene)-2-methylpropane-2-sulfinamideHCID 178418255HCID 178418255, compound

Product 1

HCID 204533024-Amino-4-phenylcyclohexan-1-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of phenyl magnesium bromide (Aldrich, 1.0 N in THF, 5.7 mL, 5.70 mmol) was added into the solution of 2-methyl-propane-2-sulfinic acid (1,4-dioxa-spiro[4.5]dec-8-ylidene)-amide (as prepared in the previous step, 1.23 g, 4.75 mmol) in THF (10 mL) at 0° C. After addition, the reaction was slowly warmed to room temperature over 2 hours. 1N HCl (5 mL) was added, and the reaction was stirred overnight. The reaction was quenched with saturated sodium bicarbonate. The solvent was removed in vacuo and the residue was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to afford the title compound as colorless oil.

Workup

  1. additionAfter addition
  2. customThe reaction was quenched with saturated sodium bicarbonate
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between DCM and water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-85cd5ae2d5154b149c7c2549c1b1fd57
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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