Water → N-(4-cyanophenyl)-5-hydroxy-3-methylpentanamide

HRID 2272559ノート

反応式

HRID 2272559 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][C:14](O)=[O:15])=[CH:5][CH:4]=1)#[N:2].B.C1COCC1.O>C1COCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:9][C:10](=[O:18])[CH2:11][CH:12]([CH3:17])[CH2:13][CH2:14][OH:15])=[CH:7][CH:8]=1)#[N:2]

参加物

5

反応物 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 3981627HCID 3981627、化合物

生成物 1

HCID 86729721N-(4-cyanophenyl)-5-hydroxy-3-methylpentanamide収率 46.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(4-cyanophenylamino)-3-methyl-5-oxopentanoic acid (1.00 g, 4.06 mmol) in THF (15 mL) was added borane-THF complex (1.2M, THF solution 6.77 mL, 8.12 mmol) under ice-cooling. The mixture was stirred at room temperature for 14 hr, and the reaction mixture was poured into water. The mixture was extracted with ethyl acetate, the organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give N-(4-cyanophenyl)-5-hydroxy-3-methylpentanamide (0.442 g, 1.904 mmol, 46.9%) as a colorless oil.

後処理

  1. temperaturecooling
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water and saturated brine
  4. customdried
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-10b1587f360f4413a634621471b8414e
出典データセット
uspto-grants-2015_09
特許番号
US09120776B2

反応ノート

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