Ethanol → 5,5-Dimethoxypiperidin-2-one

HRID 1586558Notes

Reaction equation

HRID 1586558 reaction equation
[NH:1]1[CH2:6][C:5](=[O:7])[CH2:4][CH2:3][C:2]1=[O:8].[CH3:9]O.[CH2:11]([OH:13])C>C(O)CO>[CH3:9][O:7][C:5]1([O:13][CH3:11])[CH2:6][NH:1][C:2](=[O:8])[CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 702EthanolHCID 887MethanolHCID 5339302,5-Piperidinedione

Product 1

HCID 117449065,5-Dimethoxypiperidin-2-one

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Piperidine-2,5-dione (A) described in a literature (J. Am. Chem. Soc., 80, 3717 (1958)) is allowed to react with a lower monoalcohol such as methanol or ethanol, or a with a diol such as ethylene glycol in the presence of an acid catalyst or dehydrating agent, and then the product is treated with an orthoester in the presence of an acid catalyst to obtain 5,5-dimethoxy-2-piperidone (B) whose carbonyl group at the 5-position is protected as an acetal. 5,5-Dimethoxy-2-piperidone (B) is subjected to hydrogen/deuterium exchange reaction using a deuterated compound in the presence of a base to obtain 3,3-dideutero-5,5-dimethoxy-2-piperidone (C), and then the resulting product is subjected to acidic hydrolysis to obtain 2,2-dideutero-5-aminolevulinic acid as a corresponding acid salt.

Sources & evidence

ORD record
ord-ed7719f12c3e46cb848c5b5d1ca850da
Source dataset
uspto-grants-1999_08
Patent number
US05945564

Reaction notes

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