Acetone → 2-{6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-yl}-propane-1,2-diol

HRID 42197Notes

Reaction equation

HRID 42197 reaction equation
[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:32])=[CH2:31])=[CH:26][N:25]=3)[CH2:20][CH2:19]2)=[N:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)=[O:35].C[N+]1([O-])CCOCC1.S([O-])([O-])=O.[Na+].[Na+].[OH2:51]>O.O.[O-][Os]([O-])(=O)=O.[K+].[K+].C(O)(C)(C)C>[CH2:1]([C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[N:25]=[CH:26][C:27]([C:30]([OH:35])([CH3:32])[CH2:31][OH:51])=[CH:28][CH:29]=3)[CH2:22][CH2:23]2)=[N:10][N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 180AcetoneHCID 962Water2×HCID 24437Sodium SulfiteHCID 82029Methyl morpholine oxideHCID 44186377HCID 44186377, compound

Product 1

HCID 441863782-{6-[4-(4-Benzyl-phthalazin-1-yl)-piperazin-1-yl]-pyridin-3-yl}-propane-1,2-diolYield 72%

Reagents, catalysts & solvents 2

HCID 53393272Potassium osmate(VI) dihydrateCatalystHCID 6386tert-ButanolSolvent

Procedure

To 1-benzyl-4-[4-(5-isopropenyl-pyridin-2-yl)-piperazin-1-yl]-phthalazine (68 mg, 0.158 mmol) is added acetone (1 mL), t-butanol (0.5 mL), and H2O (0.5 mL). To this suspension is then added potassium osmate (VI) dihydrate (536 μg, 1.58 μM), and NMO (21 mg, 0.174 mmol), and the reaction is stirred at room temperature for 3 h. Sodium sulfite (350 mg) is added to the resulting clear orange solution and the mixture is stirred for 1 h. Additional H2O (25 mL) is added, and the organics extracted with EtOAc (3×25 mL), dried over MgSO4, and concentrated. Purification by flash chromatography on silica gel (90:10 CH2Cl2:MeOH) afforded a clear oil which was then triturated with EtOAc to afford the title compound as a white powder (52 mg, 72% yield).

Workup

  1. extractionthe organics extracted with EtOAc (3×25 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by flash chromatography on silica gel (90:10 CH2Cl2:MeOH)
  5. customafforded a clear oil which
  6. customwas then triturated with EtOAc

Sources & evidence

ORD record
ord-009f8c573ce6455c8b254aa7822ef177
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

Loading…