tert-Butanol → 2-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-propane-1,2-diol

HRID 42196Notes

Reaction equation

HRID 42196 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]=[N:28]C(C(C)=C)=[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.C[N+]1([O-])CC[O:37]CC1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>CC(C)=O.O>[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]=[N:28][C:42]([C:41]([OH:45])([CH3:44])[CH2:43][OH:37])=[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

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 82029Methyl morpholine oxideHCID 592405284-(4-Benzyl-phthalazin-1-yl)-5'-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl

Product 1

HCID 592406692-[4-(4-Benzyl-phthalazin-1-yl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazinyl-5'-yl]-propane-1,2-diolYield 92%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

Dissolve 4-(4-Benzyl-phthalazin-1-yl)-5′-isopropenyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (100 mg, 0.237 mmol) in acetone (1.5 mL), t-Butanol (0.7 mL) and water (0.7 mL). Add K2OsO4 (0.79 mg, 0.0024 mmol) then NMO (30.5 mg, 0.26 mmol) and stir reaction for 16 h at room temperature. Quench with saturated sodium sulfite (1 mL) and extract with EtOAc. The residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2) to afford the title compound (100 mg, 92%).

Workup

  1. customreaction for 16 h at room temperature
  2. customQuench with saturated sodium sulfite (1 mL)
  3. extractionextract with EtOAc
  4. customThe residue is purified by flash chromatography on silica gel (MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-52f26fdb03c5426bb2f33ee6110b61bc
Source dataset
uspto-grants-2013_09
Patent number
US08536168B2

Reaction notes

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