Sodium Bicarbonate → 4-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester

HRID 2047638Notes

Reaction equation

HRID 2047638 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][NH:9][C:8](=[O:12])[CH2:7]1)=[O:5])[CH3:2].F[B-](F)(F)F.[CH3:18][O+](C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]=[C:8]([O:12][CH3:18])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 18699051Ethyl 2-oxopiperidine-4-carboxylate

Product 1

HCID 672974184-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add 2-oxopiperidine-4-carboxylic acid ethyl ester (6.0 g, 35 mmol) to a solution of trimethyloxonium tetrafluoroborate (9.0 g, 59.6 mmol) in dichloromethane (78 mL) cooled to 0° C. Stir the reaction for 3 hours and pour into an ice cold solution of saturated aqueous sodium bicarbonate. Separate layers and extract the aqueous layer with additional dichloromethane. Combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to afford the title compound which was used without further purification (5.87 g, 90%). Mass spectrum (m/z): 186 (M+1).

Workup

  1. customthe reaction for 3 hours
  2. extractionSeparate layers and extract the aqueous layer with additional dichloromethane
  3. dry with materialdry over anhydrous sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-16b0ec4e9c0946c99df2d2b2cdf2ec10
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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