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

HRID 2272559노트

반응식

HRID 2272559 반응식
[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]

참가 물질

5

반응물 3

HCID 962WaterHCID 2723981Borane;tetrahydrofuranHCID 3981627HCID 3981627, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-10b1587f360f4413a634621471b8414e
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120776B2

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