D-Tartaric acid → L-Malic Acid
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
Product 1
Reagents, catalysts & solvents 1
Procedure
One of the intermediates, (S)-1-methyl-3-pyrrolidinol, was synthetized 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
- customThe resulting crystals, after one recrystallization
Sources & evidence
- ORD record
- ord-3facba9af3ca4dc89a1396be78296749
- Source dataset
- uspto-grants-1988_02
- Patent number
- US04727152
Reaction notes
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