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

HRID 1826461Notes

Reaction equation

HRID 1826461 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 mmol) 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 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 vacuo
  6. customThe crude residue was chromatographed on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-56453b2f1e544a7e886a8d1ba2a253ca
Source dataset
uspto-grants-2006_05
Patent number
US07049444B2

Reaction notes

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