Dibutyltin dichloride → HCID 20775745, compound

HRID 1015641Notes

Reaction equation

HRID 1015641 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].[CH:17]([CH:19]1[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])[CH2:21][CH2:20]1)=O.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>C1COCC1.CCOC(C)=O>[CH2:28]([O:27][C:25]([N:22]1[CH2:23][CH2:24][CH:19]([CH2:17][NH:10][C:9]2[CH:8]=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[CH2:20][CH2:21]1)=[O:26])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylateHCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 20775745HCID 20775745, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (0.70 g, 3 mmol) and 4-formyl N-Cbz-piperidine (0.74 g, 3 mmol) in THF (1.2 mL) was treated with dibutyltin dichloride (46 mg, 0.15 mol) followed by phenylsilane (0.41 mL, 3.3 mmol). The mixture was stirred for 2 days at room temperature. The solvent was then evaporated and the residue was purified by silica gel column chromatography using CH2Cl2:hexanes:EtOAc as eluent to provide 4-[(2-Methoxycarbonyl-5-phenyl-thiophen-3-ylamino)-methyl]-piperidine-1-carboxylic acid-benzyl ester (0.6906 g, 50% yield).

Workup

  1. customThe solvent was then evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-725961171c1848a6b38fa1149c1b4b04
Source dataset
uspto-grants-2011_07
Patent number
US07985769B2

Reaction notes

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