Dibutyltin dichloride → 5-Cyclohex-1-enyl-3-[(3-oxo-octahydro-indolizin-7-yl)-amino]-thiophene-2-carboxylic acid methyl ester

HRID 2099628노트

반응식

HRID 2099628 반응식
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[O:17]=[C:18]1[N:26]2[CH:21]([CH2:22][C:23](=O)[CH2:24][CH2:25]2)[CH2:20][CH2:19]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:23]1[CH2:22][CH:21]2[N:26]([C:18](=[O:17])[CH2:19][CH2:20]2)[CH2:25][CH2:24]1)=[O:4]

참가 물질

6

반응물 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 12345000Hexahydroindolizine-3,7-dioneHCID 577954015-Cyclohex-1-enyl-3-aminothiophene-2-carboxylic acid methyl ester

생성물 1

HCID 577954965-Cyclohex-1-enyl-3-[(3-oxo-octahydro-indolizin-7-yl)-amino]-thiophene-2-carboxylic acid methyl ester수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-cyclohex-1-enyl-3-aminothiophene-2-carboxylic acid methyl ester (689 mg, 2.90 mmol) and 3-oxo-octahydro-indolizin-7-one (750 mg, 4.90 mmol; prepared as described in Tetrahedron, 1975, 1437) in 3 mL of dry THF was added dibutyltin dichloride (88 mg, 0.29 mmol), and the mixture was stirred for 10 min at room temperature under nitrogen. Then phenylsilane (394 μL, 3.19 mmol) was added, and the mixture was stirred overnight at room temperature. Solvent was evaporated under reduced pressure, and the residue was purified by column chromatography on silica gel using gradient 30-100% EtOAc in hexane to afford 973 mg (90%) of 5-cyclohex-1-enyl-3-[(3-oxo-octahydro-indolizin-7-yl)-amino]-thiophene-2-carboxylic acid methyl ester.

후처리

  1. stirringthe mixture was stirred overnight at room temperature
  2. customSolvent was evaporated under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel using gradient 30-100% EtOAc in hexane

출처 및 근거

ORD 기록
ord-6646f6585706467985fe887724d83850
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07569600B2

반응 노트

불러오는 중…