(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline → Solifenacin

HRID 1171852

反応式

HRID 1171852 の反応式
[O-]CC.[Na+].[C:5](=[O:18])([O:9][C@@H:10]1[CH:15]2[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]2)[CH2:11]1)OCC.[C:19]1([C@H:25]2[C:34]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:28][CH2:27][NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1(C)C=CC=CC=1.CN(C=O)C>[CH:22]1[CH:21]=[CH:20][C:19]([C@@H:25]2[N:26]([C:5]([O:9][C@@H:10]3[CH:15]4[CH2:14][CH2:13][N:12]([CH2:17][CH2:16]4)[CH2:11]3)=[O:18])[CH2:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:34]2=3)=[CH:24][CH:23]=1

参加物

6

反応物 3

HCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinolineHCID 2723922Sodium ethoxideHCID 38988498ethyl (R)-quinuclidin-3-yl carbonate

生成物 1

HCID 154059Solifenacin収率 12.1%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6228Dimethylformamide溶媒

実験手順

In a mixture of 10 ml of toluene and 0.5 ml of DMF and in the presence of 0.21 g of sodium ethoxide, 1.00 g of ethyl (R)-quinuclidin-3-yl carbonate and 1.05 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline were stirred for 7 hours while evaporating the solvent, 20 ml of toluene and 20 ml of water were added thereto, and the thus obtained organic layer was washed with 20 ml of water and then mixed with 15 ml of 1 M hydrochloric acid aqueous solution. A 30 ml portion of EtOAc and 1 M sodium hydroxide aqueous solution were added to the obtained water layer. The thus obtained organic layer was dried with sodium sulfate, concentrated under a reduced pressure and then dried, and the thus obtained solid was purified by a silica gel column chromatography to obtain 0.22 g of solifenacin.

後処理

  1. customwhile evaporating the solvent, 20 ml of toluene and 20 ml of water
  2. additionwere added
  3. washthe thus obtained organic layer was washed with 20 ml of water
  4. additionmixed with 15 ml of 1 M hydrochloric acid aqueous solution
  5. additionA 30 ml portion of EtOAc and 1 M sodium hydroxide aqueous solution were added to the obtained water layer
  6. dry with materialThe thus obtained organic layer was dried with sodium sulfate
  7. concentrationconcentrated under a reduced pressure
  8. customdried
  9. customthe thus obtained solid was purified by a silica gel column chromatography

出典と根拠

ORDレコード
ord-6a8a0493e2174174ad99fdd286b8d864
出典データセット
uspto-grants-2010_11
特許番号
US07829715B2

関連ノート

読み込み中…