Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate → Methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate

HRID 453542노트

반응식

HRID 453542 반응식
[C:1]([O:5][C:6](=[O:27])[CH2:7][C:8]1[CH:24]=[CH:23][C:11]([O:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][CH:14]=2)=[C:10]([C:25]#[N:26])[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>N.CO.[Ni]>[NH2:26][CH2:25][C:10]1[CH:9]=[C:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])[CH:24]=[CH:23][C:11]=1[O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][CH:22]=1

참가 물질

4

반응물 1

HCID 68466372Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate

생성물 1

HCID 68464831Methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate수율 62.8%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 21705897Ammonia methanol용매

실험 절차

To a stirred solution of the methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-cyanophenoxy)benzoate (1.086 mg, 2.96 mmol) in 7N ammonia/methanol (30 ml) under nitrogen was added Raney Nickel (25.3 mg, 0.296 mmol). The reaction was purged with a hydrogen balloon and stirred under hydrogen overnight. The reaction was filtered through GF paper and the solid catalyst was rinsed with methanol and ethyl acetate. The filtrate was concentrated, and the crude product was purified by silica gel chromatography to give methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate (0.69 g).

후처리

  1. customThe reaction was purged with a hydrogen balloon
  2. filtrationThe reaction was filtered through GF paper
  3. washthe solid catalyst was rinsed with methanol and ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customthe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-c8ec6934a1644c05981507c4df3dc4cb
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492437B2

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