(3R)-1-methylpiperidin-3-ol → Oxo-thiophen-2-yl-acetic acid (R)-1-methyl-piperidin-3-yl ester

HRID 551378Notes

Reaction equation

HRID 551378 reaction equation
[O:1]=[C:2]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[C:3](Cl)=[O:4].[CH3:11][N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([OH:18])[CH2:13]1>C(Cl)Cl>[CH3:11][N:12]1[CH2:17][CH2:16][CH2:15][C@@H:14]([O:18][C:3](=[O:4])[C:2](=[O:1])[C:6]2[S:7][CH:8]=[CH:9][CH:10]=2)[CH2:13]1

Participants

4

Reactant 2

HCID 6994421(3R)-1-methylpiperidin-3-olHCID 117451372-Chloro-1-(2-thienyl)-2-oxo-1-ethanone

Product 1

HCID 67194971Oxo-thiophen-2-yl-acetic acid (R)-1-methyl-piperidin-3-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxo-thiophen-2-yl-acetyl chloride (8.9 g, 51.2 mmol) at 5° C. in DCM (50 ml) is added a solution of (R)-1-Methyl-piperidine-3-ol (5.87 g, 51 mmol) in DCM (50 ml), dropwise with stirring over 20 minutes. The resulting mixture is stirred for 18 hours at room temperature. Washing with 1 Molar sodium bicarbonate solution, drying over magnesium sulphate, filtration and evaporation then gives the title compound as a dark oil.

Workup

  1. stirringThe resulting mixture is stirred for 18 hours at room temperature
  2. washWashing with 1 Molar sodium bicarbonate solution
  3. dry with materialdrying over magnesium sulphate, filtration and evaporation

Sources & evidence

ORD record
ord-dc1225d1dfc04e0e84b6232920bee8be
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Reaction notes

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