Methanol → 3-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol

HRID 633835ノート

反応式

HRID 633835 の反応式
C[N+]1([O-])CC[O:5]CC1.[CH2:9]([C:12]1[C:13]([Cl:24])=[CH:14][N:15]=[C:16]2[C:21]=1[N:20]=[C:19]([O:22][CH3:23])[CH:18]=[CH:17]2)[CH:10]=C.[CH3:25][OH:26]>ClCCl.O.O.O.[Os](=O)(=O)=O.[K]>[Cl:24][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[CH2:9][CH:10]([OH:5])[CH2:25][OH:26])=[N:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2

参加物

7

反応物 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 671828908-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine

生成物 1

HCID 671805623-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol収率 96%

試薬・触媒・溶媒 3

HCID 178526964HCID 178526964、化合物触媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

N-Methylmorpholine-N-oxide (0.76 g, 64.0 mmol, 1.5 eq) is added at room temperature to a stirred solution of 8-allyl-7-chloro-2-methoxy-[1,5]naphthyridine (1.0 g, 4.26 mmol, 1.0 eq) in dichloromethane (40 mL) and water (4 mL), followed by potassium osmium(VI) oxide dihydrate (80 mg, 0.23 mmol, 0.05 eq). After 16 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium sulfite aqueous solution (20 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 40:1, v/v) to afford 3-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol as a light yellow solid (1.1 g, 96% yield).

後処理

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

出典と根拠

ORDレコード
ord-f9131a8b54c74f4980b72c37781675c1
出典データセット
uspto-grants-2016_04
特許番号
US09321788B2

反応ノート

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