2-Methyl-3-oxobutanoic acid → 3-Hydroxyhexanoic acid, (3R)-
Reaction equation
[O:1]=[C:2]([CH2:7][CH2:8][CH3:9])[CH2:3][C:4]([OH:6])=[O:5].CC(C(=O)C)C(O)=O>>[OH:1][C@H:2]([CH2:7][CH2:8][CH3:9])[CH2:3][C:4]([OH:6])=[O:5]Participants
3
Procedure
In accordance with the procedure of Example 9, ethyl ester of 3-oxohexanoic acid as a substrate in place of ethyl ester of 2-methyl-3-oxobutyric acid was subjected to reduction by baker's yeast to obtain ethyl ester of (3R)-3-hydroxyhexanoic acid. This compound was subjected to methylation according to the process of the literature [G. Frater et al., Tetrahedron, 40, 1269 (1984)] as in Reference Example 3, to obtain ethyl ester of (2R, 3R)-3-hydroxy-2-methylhexanoic acid. This compound was converted to a methyl ether compound and then subjected to hydrolysis in accordance with the procedure of Example 11 to obtain the title compound.
Sources & evidence
- ORD record
- ord-4226c25948484b0ba9c72dc88815f1e8
- Source dataset
- uspto-grants-1992_12
- Patent number
- US05167863
Reaction notes
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