Water → 2-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-propane-1,2-diol

HRID 1480007Notes

Reaction equation

HRID 1480007 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[N:24]C(C(C)=C)=[CH:22][N:21]=3)[C@H:16]([CH3:29])[CH2:15]2)=[C:10]([CH3:30])[C:9]=1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32]([OH:36])([CH3:35])([CH3:34])[CH3:33].O.C[N+]1([O-])CC[O:42]CC1>CC(C)=O>[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[N:24][C:33]([C:32]([OH:36])([CH3:35])[CH2:34][OH:42])=[CH:22][N:21]=3)[C@H:16]([CH3:29])[CH2:15]2)=[C:10]([CH3:30])[C:9]=1[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 59191459(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5'-isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Product 1

HCID 451071762-[(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-propane-1,2-diolYield 38%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

(R)-4-(6-Benzyl-4,5-dimethyl-pyridazin-3-yl)-5′-isopropenyl-2-methyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (example 143, 120 mg, 0.290 mmol) is suspended in acetone (2 mL), tert-butanol (1 mL), and H2O (1 mL). To this suspension is added K2OsO4 (9.6 mg, 0.029 mmol) and NMO (37.4 mg, 0.319 mmol). The reaction is stirred at room temperature for 16 h. Concentrate in vacuo. Add H2O and extract with EtOAc. Wash the combined organics with brine and concentrate in vacuo. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (49.2 mg, 38%).

Workup

  1. concentrationConcentrate in vacuo
  2. extractionAdd H2O and extract with EtOAc
  3. washWash the combined organics with brine
  4. concentrationconcentrate in vacuo
  5. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-dbaa112478c0492c902bc2c9eaea052d
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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