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

HRID 1190008Notes

Reaction equation

HRID 1190008 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-99c9f5b149174ae7b83f0aba36d5ded4
Source dataset
uspto-grants-2014_03
Patent number
US08674118B2

Reaction notes

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