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Sodium borohydride → Methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylate

HRID 887757
ノート
印刷プレビュー

反応式

HRID 887757 の反応式
[CH2:1]([N:8]([CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[C:12](/[CH:19]=[CH:20]/[C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.[Cl-].[NH4+].O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:25]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:9]1[N:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]([CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:11][CH:10]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=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 2

HCID 4311764Sodium borohydrideHCID 59145876methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate

生成物 1

HCID 59145865Methyl 6-(dibenzylamino)-3-(3-methoxy-3-oxopropyl)pyridine-2-carboxylate収率 86%

試薬・触媒・溶媒 3

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒
HCID 25517Ammonium Chloride溶媒

実験手順

To a solution of methyl 6-(dibenzylamino)-3-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]pyridine-2-carboxylate (2.60 g, 6.24 mmol) and nickel(II) chloride hexahydrate (891 mg, 3.75 mmol) in methanol (62 mL) was added sodium tetrahydroborate (472 mg, 12.5 mmol) under ice-cooling, and the mixture was stirred for 5 min. The reaction solution was diluted with saturated aqueous ammonium chloride solution, and the organic solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70) to give the title compound (2.24 g, yield 86%).

後処理

  1. temperaturecooling
  2. customthe organic solvent was evaporated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=10/90→30/70)

出典と根拠

ORDレコード
ord-42093bc147ea48df87675a44b529ea9e
出典データセット
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08247429B2

反応ノート

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