D-Tartaric acid → L-Malic Acid

HRID 1193761Notes

Reaction equation

HRID 1193761 reaction equation
[C@@H:1]([OH:10])([C:7]([OH:9])=[O:8])[C@H:2](O)[C:3]([OH:5])=[O:4]>CO>[C:7]([OH:9])(=[O:8])[C@H:1]([CH2:2][C:3]([OH:5])=[O:4])[OH:10]

Participants

3

Reactant 1

HCID 439655D-Tartaric acid

Product 1

HCID 222656L-Malic Acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

One of the intermediates, (S)-1-methyl-3-pyrrolidinol, was synthesized with retention of optical purity as shown in Chart IX starting with (S)-malic acid. The (S)-1-methyl-3-pyrrolidinol was shown to be dextrorotatory. As an alternative method of obtaining the resolved isomers of 1-methyl-3-pyrrolidinol, the racemic mixture was treated with (2S,3S)-tartaric acid in methanol. The resulting crystals, after one recrystallization, were converted to the base. This base was the dextrorotatory (S)-1-methyl-3-pyrrolidinol identical to that produced from (S)-malic acid.

Workup

  1. customThe resulting crystals, after one recrystallization

Sources & evidence

ORD record
ord-66f2bd8bec1f40ab84950503804980c7
Source dataset
uspto-grants-1989_03
Patent number
US04810795

Reaction notes

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