Cyclohexane → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

HRID 2219868Notes

Reaction equation

HRID 2219868 reaction equation
[CH3:1][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[C@H:15]([OH:24])[CH2:16][C@H:17]([OH:23])[CH2:18][C:19]([O:21]C)=[O:20])=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].C1CCCCC1.[OH-].[Na+:39]>CO>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:24])[CH2:16][CH:17]([OH:23])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:39]

Participants

5

Reactant 3

HCID 8078Cyclohexane2×HCID 14798Sodium HydroxideHCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to cyclohexane (60 ml) and the slurry was heated to reflux. A solution of NaOH (1 eq.) in MeOH (3 ml) was added to the slurry solution which became clear. After 15 min. a precipitate formed. After another hour, the mixture was cooled to room temperature and cyclohexane (40 ml) was added. The mixture was stirred over night. The product was isolated by filtration under nitrogen, washed with cyclohexane (90 ml) and dried at 50° C. in a vacuum oven for 24 h to yield 2.73 g (90%) of amorphous fluvastatin sodium.

Workup

  1. temperaturethe slurry was heated to reflux
  2. customAfter 15 min. a precipitate formed
  3. waitAfter another hour
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with cyclohexane (90 ml)
  6. customdried at 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-76372360c0834b3bbc0d659602520372
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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