Lovastatin → HCID 20678451, compound

HRID 987056Notes

Reaction equation

HRID 987056 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:5]([O:7][C@@H:8]1[C@@H:13]2[C@@H:14]([CH2:19][CH2:20][C@H:21]3[O:27][C:25](=[O:26])[CH2:24][C@H:23]([OH:28])[CH2:22]3)[C@@H:15]([CH3:18])[CH:16]=[CH:17][C:12]2=[CH:11][C@H:10]([CH3:29])[CH2:9]1)=[O:6])[CH3:4].[BH4-].[Li+]>C(O)C>[CH3:29][CH:10]1[CH:11]=[C:12]2[CH:13]([CH:14]([CH2:19][CH2:20][CH:21]([OH:27])[CH2:22][CH:23]([OH:28])[CH2:24][CH2:25][OH:26])[CH:15]([CH3:18])[CH:16]=[CH:17]2)[CH:8]([O:7][C:5](=[O:6])[CH:3]([CH3:4])[CH2:2][CH3:1])[CH2:9]1

Participants

4

Reactant 2

HCID 53232LovastatinHCID 4148881Lithium borohydride

Product 1

HCID 20678451HCID 20678451, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 65 mg (0.15 mmol) of mevinolin in 5 ml of ethanol are added 22 mg (1.0 mmol) lithium borohydride and the resulting mixture is stirred overnight at room temperature. The reaction is quenched with 0.1 N aqueous HCl. The phases are separated and the aqueous phase is extracted twice with ethyl acetate. The organic phases are combined, washed with brine and dried over sodium sulfate. The solvent is evaporated and the crude product purified by silica gel chromatography (ethyl acetate) to afford 2-methyl-butyric acid 3,7-dimethyl-8-(3,5,7-trihydroxy-heptyl)-1,2,3,7,8,8a-hexahydro-naphthalen-1-yl ester as an oil.

Workup

  1. customThe reaction is quenched with 0.1 N aqueous HCl
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is evaporated
  7. customthe crude product purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-cc13772271924698bb1ed2e34dd75fdd
Source dataset
uspto-grants-2003_10
Patent number
US06630492B1

Reaction notes

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