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

HRID 1171852

반응식

HRID 1171852 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 154059Solifenacin수율 12.1%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6a8a0493e2174174ad99fdd286b8d864
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829715B2

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