Diethylmethoxyborane → HCID 131720247, compound

HRID 1600353Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11](=[O:20])[CH2:12][C@@H:13]([OH:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16].C(B(CC)OC)C.[BH4-].[Na+]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C@@H:11]([OH:20])[CH2:12][C@@H:13]([OH:19])[CH2:14][C:15]([O:17][CH3:18])=[O:16]

Participants

Reactant 3

HCID 522516Diethylmethoxyborane

HCID 4311764Sodium borohydride

HCID 86751393HCID 86751393, compound

Product 1

HCID 131720247HCID 131720247, compound

Procedure

For instance, methyl (3R,6E)-3-[(tert-butyldimethylsilyl)oxy]-7-(2,4-dichlorophenyl)-5-oxo-6-heptenoate (which is one of the compounds of the formula (1)) is subjected to the tert-butyldimethylsilyl removing step using hydrogen fluoride in the manner as described in Japanese Patent Provisional Publication H5(1993)-178841, to give methyl (3R, 6E)-7-(2,4-dichlorophenyl)-3-hydroxy-5-oxo-6-heptenoate. The obtained ester is then subjected to Syn reduction using diethylmethoxyborane and sodium borohydride (NaBH4), to give methyl (3R,5S,6E)-7-(2,4-dichlorophenyl)-3,5-dihydroxy-6-heptenoate. Subsequently, thus obtained ester is treated with sodium hydroxide and hydrochloric acid in the manner as described in Journal of Medicinal Chemistry, 1985, vol.28, No.3, pp.347-358, to give (+)-trans-(E)-6-[2-(2,4-dichlorophenyl)-ethenyl] 3,4,5,6-tetrahydro-4-hydroxy-2H-pyran-2-on which has the 3-hydroxy-3-methylglutaryl Coenzyme A reductase preventive action.

Sources & evidence

ORD record: ord-507bc9417921429eaa77edb79de6fc2d
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05744604

Reaction notes

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