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

HRID 541216ノート

反応式

HRID 541216 の反応式
[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]

参加物

5

反応物 2

HCID 68288828tert-butyl 5-(4-cyanophenyl)-2,3,4,7-tetrahydro-1H-azepine-1-carboxylate2 回HCID 68288921tert-butyl 4-(4-cyanophenyl)-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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%)

出典と根拠

ORDレコード
ord-56a6a30c6025463cae99f8cfdfec9a05
出典データセット
uspto-grants-2014_10
特許番号
US08871790B2

反応ノート

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