tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate → Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

HRID 541216노트

반응식

HRID 541216 반응식
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:10][CH2:11][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13][CH2:14][CH:15]=2)=[CH:5][CH:4]=1)#[N:2].C(C1C=CC(C2CCCN(C(OC(C)(C)C)=O)CC=2)=CC=1)#N>[Pd].C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[CH2:15][CH2:14][CH2:13][N:12]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:11][CH2:10]2)=[CH:7][CH:8]=1)#[N:2]

참가 물질

5

반응물 2

HCID 68288828tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate2회HCID 68288921tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

생성물 1

HCID 68288974Tert-butyl 4-(4-cyanophenyl)azepane-1-carboxylate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 8857Ethyl Acetate용매

실험 절차

To a 25 mL round bottom flask containing a mixture of tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate and tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate (compound 40.2, 167 mg, 0.56 mmol) was added 10% palladium on carbon (40 mg) and ethyl acetate (6 mL). The system was purged with nitrogen then charged with hydrogen and stirred at room temperature. After purging the system with nitrogen, the mixture was filtered through celite and the filtrate was concentrated. The residue was purified by preparative TLC to obtain a colorless wax (77 mg, 45%). m/z (ES+) 245 (M minus t-butyl+H)+.

후처리

  1. additionTo a 25 mL round bottom flask containing
  2. customThe system was purged with nitrogen
  3. additionthen charged with hydrogen
  4. customAfter purging the system with nitrogen
  5. filtrationthe mixture was filtered through celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by preparative TLC
  8. customto obtain a colorless wax (77 mg, 45%)

출처 및 근거

ORD 기록
ord-56a6a30c6025463cae99f8cfdfec9a05
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871790B2

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