Paper Report for: Furutani_2002_J.Org.Chem_67_4599
Reference
Title: A practical procedure for the large-scale preparation of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate, a key intermediate for diltiazem Furutani T, Imashiro R, Hatsuda M, Seki M Ref: J Org Chem, 67:4599, 2002 : PubMed
A practical synthesis of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate (-)-2, a key intermediate for diltiazem (1), was developed. Treatment of methyl (E)-4-methoxycinnamate 3 with chiral dioxirane, generated from chiral ketone 4, provided (-)-2 in 77% ee and 89% yield. The crude mixture of (-)-2 and 4 was efficiently separated by the use of novel and simple equipment performing a lipase-catalyzed transesterification and a continuous dissolution and crystallization to furnish the optically pure (-)-2 and recovery of 4 in 74% and 91% yield, respectively.
        
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Furutani T, Imashiro R, Hatsuda M, Seki M (2002) A practical procedure for the large-scale preparation of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate, a key intermediate for diltiazem J Org Chem67: 4599-601
Furutani T, Imashiro R, Hatsuda M, Seki M (2002) J Org Chem67: 4599-601