Hydrochloric Acid → 3-hexyl-6-[3-(1H-imidazol-5-yl)phenyl]-6-methyl-3-azabicyclo[3.1.0]hexan-2-one

HRID 428950Notes

Reaction equation

HRID 428950 reaction equation
[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([CH3:43])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[N:23](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:22]=[N:21][CH:20]=3)[CH:14]=2)[C:8]1=[O:44])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].Cl.C(=O)([O-])O.[Na+].ClCCl>CO>[CH2:1]([N:7]1[CH2:12][CH:11]2[CH:9]([C:10]2([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]3[NH:23][CH:22]=[N:21][CH:20]=3)[CH:14]=2)[CH3:43])[C:8]1=[O:44])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 516892Sodium BicarbonateHCID 221411573-Hexyl-6-methyl-6-[3-(1-triphenylmethyl-1H-imidazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one

Product 1

HCID 221412213-hexyl-6-[3-(1H-imidazol-5-yl)phenyl]-6-methyl-3-azabicyclo[3.1.0]hexan-2-oneYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-hexyl-6-methyl-6-[3-(1-triphenylmethyl-1H-imidazol-5-yl)phenyl]-3-azabicyclo[3.1.0]hexan-2-one (Preparation 74, 55 mg, 0.95 nmmol) in methanol (1.5 ml) was added aqueous hydrochloric acid (2M, 0.5 ml) and the mixture was heated under reflux for 16 h. The reaction mixture was then cooled to room temperature and poured onto solid sodium hydrogen carbonate. Dichloromethane was added, the layers were separated and the organic extracts were dried (MgSO4) and concentrated in in vacuo. The crude residue was chromatographed on silica gel eluting with ethyl acetate to give the title compound as a clear oil (21 mg, 66%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 16 h
  3. customthe layers were separated
  4. dry with materialthe organic extracts were dried (MgSO4)
  5. concentrationconcentrated in in vacuo
  6. customThe crude residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-10d7ed91c1464deeb3cbf06b094c6733
Source dataset
uspto-grants-2001_11
Patent number
US06313312B1

Reaction notes

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