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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 1480007
ノート
印刷プレビュー

反応式

HRID 1480007 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 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-diol収率 38%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

(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%).

後処理

  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)

出典と根拠

ORDレコード
ord-dbaa112478c0492c902bc2c9eaea052d
出典データセット
uspto-grants-2016_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09409871B2

反応ノート

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