Diethyl Ether → Methyl 2-(1-methyl-3-(5-phenethylfuran-2-carboxamido)piperidin-3-yl)acetate

HRID 1192898Notes

Reaction equation

HRID 1192898 reaction equation
[NH2:1][C:2]1([CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH2:7][CH2:6][CH2:5][N:4]([CH3:8])[CH2:3]1.[CH2:14]([C:22]1[O:26][C:25]([C:27](ON2C(=O)CCC2=O)=[O:28])=[CH:24][CH:23]=1)[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C.C(OCC)C>CN(C=O)C>[CH3:8][N:4]1[CH2:5][CH2:6][CH2:7][C:2]([CH2:9][C:10]([O:12][CH3:13])=[O:11])([NH:1][C:27]([C:25]2[O:26][C:22]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:23][CH:24]=2)=[O:28])[CH2:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 66864584Methyl 2-(3-amino-1-methylpiperidin-3-yl)acetateHCID 866498432,5-Dioxopyrrolidin-1-yl 5-phenethylfuran-2-carboxylate

Product 1

HCID 66864596Methyl 2-(1-methyl-3-(5-phenethylfuran-2-carboxamido)piperidin-3-yl)acetateYield 89.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-(3-amino-1-methylpiperidin-3-yl)acetate (37 mg, 0.2 mmol) and 2,5-dioxopyrrolidin-1-yl 5-phenethylfuran-2-carboxylate (75 mg, 0.24 mmol) in DMF (1 mL) was treated with triethylamine (0.11 μL, 0.8 mmol) and stirred at room temperature for 18 h. Diethyl ether (20 mL) was added and the resulting white precipitate was collected and purified by silica gel chromatography (elution 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2) to give the title compound as a white powder (69 mg, 87%). MS ESI 385.2 [M+H]+, calcd for [C22H28N2O4+H] 385.20.

Workup

  1. customthe resulting white precipitate was collected
  2. custompurified by silica gel chromatography (elution 5% MeOH/CH2Cl2 to 10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-2f6964a8450443ea9fc2c31827c92c61
Source dataset
uspto-grants-2014_03
Patent number
US08680282B2

Reaction notes

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