Acetone → Ammonia

HRID 1878790Notes

Reaction equation

HRID 1878790 reaction equation
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:23][CH:22]=[CH:21][CH2:20]3)[CH2:14][CH2:13]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[OH2:24].C[N+]1([O-])CCOCC1.CC(C)=O.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].[OH2:46]>O.O.[O-][Os]([O-])(=O)=O.[K+].[K+]>[NH3:5].[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([O:11][CH:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH:19]3[CH2:23][CH:22]([OH:24])[CH:21]([OH:46])[CH2:20]3)[CH2:14][CH2:13]2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

8

Reactant 5

HCID 180AcetoneHCID 962Water2×HCID 656671Sodium PyrosulfiteHCID 2724197N-Methylmorpholine N-oxide monohydrateHCID 66615625HCID 66615625, compound

Product 2

HCID 222AmmoniaHCID 66615645HCID 66615645, compound

Reagents, catalysts & solvents 1

HCID 53393272Potassium osmate(VI) dihydrateCatalyst

Procedure

2-Chloro-4-(1-cyclopent-3-enylmethyl-piperidin-4-yloxy)-3-methyl-benzonitrile (1.5 g), potassium osmate (vi) dihydrate (0.042 g) and 4-methylmorpholine 4-oxide monohydrate (3.2 ml of a 50% soln in water) were added to acetone (40 ml) and water (5 ml). The reaction mixture was heated under reflux for 1 h. LC/MS showed complete conversion to the desired diol. The reaction was allowed to cool to room temperature and then sodium metabisulfite solution was added. The reaction mixture was extracted with dichloromethane, then sodium bicarbonate solution was added and the aqueous mixture was extracted again with dichloromethane. The organic extracts were combined and evaporated. The residue was loaded onto an SCX cartridge and eluted with dichloromethane/methanol and then with 0.7M ammonia in methanol to give the title compound (1.3 g).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 1 h
  3. extractionThe reaction mixture was extracted with dichloromethane
  4. additionsodium bicarbonate solution was added
  5. extractionthe aqueous mixture was extracted again with dichloromethane
  6. customevaporated
  7. washeluted with dichloromethane/methanol

Sources & evidence

ORD record
ord-3b48c925684d49caa05275b1c8380a26
Source dataset
uspto-grants-2012_11
Patent number
US08314127B2

Reaction notes

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