Dibutyltin dichloride → Benzyl 4-(2-(methoxycarbonyl)-5-phenylthiophen-3-ylamino)piperidine-1-carboxylate

HRID 1923487Notes

Reaction equation

HRID 1923487 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].O=[C:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[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[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:25])[CH2:20][CH2:19]1)=[O:4]

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 643496Benzyl 4-oxopiperidine-1-carboxylateHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Product 1

HCID 58423010Benzyl 4-(2-(methoxycarbonyl)-5-phenylthiophen-3-ylamino)piperidine-1-carboxylateYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (2.33 g, 10 mmol) in THF (2.0 mL) was added benzyl 4-oxopiperidine-1-carboxylate (2.33 g, 10 mmol), dibutyltin chloride (302 mg, 1.0 mmol) and phenylsilane (1.36 ml, 11 mmol) at room temperature. The reaction mixture was stirred for two days at room temperature and quenched with saturated NaHCO3 aqueous solution. The mixture was extracted with ethyl acetate and washed with brine. Dried and concentrated, the crude was purified on silica gel column to give the title compound (4.23 g, 94%).

Workup

  1. customquenched with saturated NaHCO3 aqueous solution
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with brine
  4. customDried
  5. concentrationconcentrated
  6. customthe crude was purified on silica gel column

Sources & evidence

ORD record
ord-901e454f122f4fc38733dace8b265555
Source dataset
uspto-grants-2012_05
Patent number
US08178531B2

Reaction notes

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