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

HRID 2047639Notes

Reaction equation

HRID 2047639 reaction equation
F[B-](F)(F)F.[CH3:6][O+](C)C.[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][NH:18][C:17](=[O:21])[CH2:16]1)=[O:14])[CH3:11].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:10]([O:12][C:13]([CH:15]1[CH2:20][CH2:19][N:18]=[C:17]([O:21][CH3:6])[CH2:16]1)=[O:14])[CH3:11]

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 esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add trimethyloxonium tetrafluoroborate (530.7 g) to a solution of 2-oxopiperidine-4-carboxylic acid ethyl ester (307.7 g, 1.80 mol) in dry dichloromethane (4.68 L) under nitrogen, and stir the reaction at room temperature for 16 hours. Cool the mixture to 0° C. and adjust to pH 8 with saturated aqueous sodium bicarbonate. Separate the layers and extract the aqueous phase with additional dichloromethane (2×1 L). Combine the organic phases, dry over magnesium sulfate, filter, and concentrate to provide the title compound (273.68 g). Mass spectrum (m/z): 186 (M+1).

Workup

  1. customthe reaction at room temperature for 16 hours
  2. customSeparate the layers
  3. extractionextract the aqueous phase with additional dichloromethane (2×1 L)
  4. dry with materialCombine the organic phases, dry over magnesium sulfate
  5. filtrationfilter
  6. concentrationconcentrate

Sources & evidence

ORD record
ord-7b188eaf71c94ea18e6929d0d5c28192
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

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