6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole → 3-Amino-2,3,4,9-tetrahydro-1H-carbazol-6-ol

HRID 843937ノート

反応式

HRID 843937 の反応式
C([O:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1)C1C=CC=CC=1.[H][H]>C(O)C.[Ni]>[OH:8][C:9]1[CH:10]=[C:11]2[C:19](=[CH:20][CH:21]=1)[NH:18][C:17]1[CH2:16][CH2:15][CH:14]([NH2:22])[CH2:13][C:12]2=1

参加物

5

反応物 2

HCID 226113086-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazoleHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 153417413-Amino-2,3,4,9-tetrahydro-1H-carbazol-6-ol収率 56%

試薬・触媒・溶媒 2

HCID 935Nickel触媒HCID 702Ethanol溶媒

実験手順

To a solution of 0.871 gm (2.98 mMol) 6-benzyloxy-3-amino-1,2,3,4-tetrahydro-9H-carbazole in 200 mL ethanol were added about 2.0 gm Raney Nickel and hydrogen introduced to the reaction mixture under balloon pressure. After stirring for 18 hours at room temperature the balloon was refilled with hydrogen and the reaction stirred an additional 3 days at room temperature. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to give a colorless solid. The residual solid was subjected to silica gel chromatography, eluting with 80:15:5 dichloromethane: methanol:ammonium hydroxide. Fractions shown to contain product were combined and concentrated under reduced pressure to give 0.335 gm (56%) of the title compound.

後処理

  1. additionintroduced to the reaction mixture under balloon pressure
  2. stirringthe reaction stirred an additional 3 days at room temperature
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customto give a colorless solid
  6. washeluting with 80:15:5 dichloromethane
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-05edafb982af4e4896811997655ecc27
出典データセット
uspto-grants-2002_04
特許番号
US06380201B1

反応ノート

読み込み中…