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

HRID 453491노트

반응식

HRID 453491 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 74%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 21705897Ammonia methanol용매

실험 절차

The product of step A (2.5 g, 6.80 mmol) was diluted with 7N ammonia/methanol (30 mL) followed by the addition of Raney Nickel (0.0583 g, 0.680 mmol). The reaction mixture was purged three times with hydrogen and stirred for 12 hours. The reaction mixture was then filtered through a GF/F filter and concentrated. The residue was purified using a biotage 40M column eluting with methylene chloride:MeOH:NH4OH (90:9:1) to yield methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate (1.87 g, 74.0% yield) as a clear oil.

후처리

  1. customThe reaction mixture was purged three times with hydrogen
  2. filtrationThe reaction mixture was then filtered through a GF/F
  3. filtrationfilter
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washeluting with methylene chloride:MeOH:NH4OH (90:9:1)

출처 및 근거

ORD 기록
ord-9d42f0ee77874b4fb9c2624419ee2c57
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492437B2

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