HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2047639Generated: October 27, 2026
Sodium Bicarbonate → 4-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester
https://huagongshe.com/reaction/2047639
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1) | HCID 2735153 | — |
| Reactant | Ethyl 2-oxopiperidine-4-carboxylate | HCID 18699051 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | 4-Pyridinecarboxylic acid, 2,3,4,5-tetrahydro-6-methoxy-, ethyl ester | HCID 67297418 | 82.1% |
Reaction Steps
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).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08592590B2 |
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| Source dataset | uspto-grants-2013_11 |
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| ORD ID | ord-7b188eaf71c94ea18e6929d0d5c28192 |
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| Source note | uspto-grants-2013_11 |
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