Dibutyltin dichloride → 4-(2-Methoxycarbonyl-thiophen-3-ylamino)-piperidine-1-carboxylic acid benzyl ester

HRID 73208

Reaction equation

HRID 73208 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4].[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Sn](CCCC)(CCCC)(Cl)Cl.C1([SiH3])C=CC=CC=1>C1COCC1>[CH2:11]([O:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([NH:10][C:9]2[CH:8]=[CH:7][S:6][C:5]=2[C:3]([O:2][CH3:1])=[O:4])[CH2:23][CH2:22]1)=[O:20])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 643496Benzyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 684248614-(2-Methoxycarbonyl-thiophen-3-ylamino)-piperidine-1-carboxylic acid benzyl esterYield 101.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reductive amination of 3-amino-thiophene-2-carboxylic acid methyl ester (3.0 g, 19.1 mmol) and 4-oxo-piperidine-1-carboxylic acid benzyl ester (4.46 g, 19.1 mmol) in THF (4.6 mL) employing Bu2SnCl2 (0.598 g, 1.92 mmol) and PhSiH3 (2.58 mL, 21.6 mmol) was carried out as described for example 19, step 1 gave 4-(2-methoxycarbonyl-thiophen-3-ylamino)-piperidine-1-carboxylic acid benzyl ester (7.25 g, quantitative). NMR 1H (CDCl3, 400 MHz): 7.4-7.3 (m, 6H), 6.9-6.78 (m, 1H), 6.7-6.6 (m, 1H), 5.14 (s, 2H), 4.15-4.0 (m, 2H), 3.81 (s, 3H), 3.6-3.45 (m), 3.1 (brt, 2H), 2.1-1.9 (m, 2H), 1.6-1.45 (m, 2H).

Sources & evidence

ORD record
ord-7cbc4f34d00440aabc26ce241c80932d
Source dataset
uspto-grants-2014_09
Patent number
US08829030B2

Linked notes

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