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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 447128
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HRID 447128 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 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

생성물 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-diol수율 38%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

(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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-660ca5ce04ad44b783911624de79c405
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08481542B2

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