Methanol → 4-(4-Benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde

HRID 1615394ノート

反応式

HRID 1615394 の反応式
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[O:19])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.CO.[Cl-].[Na+]>ClCCl>[CH2:21]([O:20][C:18]([NH:17][CH:14]1[CH2:13][CH2:12][N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH:4]=[O:3])=[CH:10][CH:9]=2)[CH2:16][CH2:15]1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

参加物

6

反応物 4

HCID 887MethanolHCID 5234Sodium ChlorideHCID 21273587HCID 21273587、化合物HCID 66691942Ethyl 4-(4-(benzyloxycarbonylamino)piperidin-1-yl)benzoate

生成物 1

HCID 866745294-(4-Benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

The 4-(4-benzyloxycarbonylaminopiperidin-1-yl)-benzoic acid ethyl ester (13.6 g, 35.6 mmol) obtained in Example 7 (2) was dissolved in dichloromethane (150 ml), and a diisobutylaluminum hydride-hexane solution (91 ml, 89.0 mmol) was added thereto, followed by stirring at −78° C. for 1 hour. Methanol was added to the reaction mixture, and then saturated sodium chloride was added thereto, followed by stirring. After the insoluble material was filtered with Celite, the solvent was evaporated from the filtrate under reduced pressure. The obtained residue was dissolved in dichloroethane (180 ml), and manganese dioxide (38.0 g) was added thereto, followed by stirring at 60° C. for 21 hours. After the insoluble material was filtered with Celite, the solvent was evaporated from the filtrate under reduced pressure, thereby obtaining 4-(4-benzyloxycarbonylaminopiperidin-1-yl)-benzaldehyde (7.0 g, 58%) as a white solid.

後処理

  1. stirringby stirring
  2. filtrationAfter the insoluble material was filtered with Celite
  3. customthe solvent was evaporated from the filtrate under reduced pressure
  4. dissolutionThe obtained residue was dissolved in dichloroethane (180 ml)
  5. additionmanganese dioxide (38.0 g) was added
  6. stirringby stirring at 60° C. for 21 hours
  7. filtrationAfter the insoluble material was filtered with Celite
  8. customthe solvent was evaporated from the filtrate under reduced pressure

出典と根拠

ORDレコード
ord-9a9aa21954f4434bba16efad3f4eb22b
出典データセット
uspto-grants-2014_07
特許番号
US08765750B2

反応ノート

読み込み中…