| Title : A practical procedure for the large-scale preparation of methyl (2R,3S)-3-(4-methoxyphenyl)glycidate, a key intermediate for diltiazem - Furutani_2002_J.Org.Chem_67_4599 |
| Author(s) : Furutani T , Imashiro R , Hatsuda M , Seki M |
| Ref : J Org Chem , 67 :4599 , 2002 |
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Abstract :
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. |
| PubMedSearch : Furutani_2002_J.Org.Chem_67_4599 |
| PubMedID: 12076164 |
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 Chem
67 :4599
Furutani T, Imashiro R, Hatsuda M, Seki M (2002)
J Org Chem
67 :4599