Methanol → HCID 86749410, compound

HRID 1720701Notes

Reaction equation

HRID 1720701 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2/[CH:21]=[CH:22]/[CH:23]([OH:32])[CH2:24][C:25](=[O:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:4][CH:3]=1.C(B(CC)CC)C.[BH4-].[Na+].CO>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:11]=[C:10]([CH3:20])[C:9]=2[CH:21]=[CH:22][CH:23]([OH:32])[CH2:24][CH:25]([OH:31])[CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 7357TriethylboraneHCID 4311764Sodium borohydrideHCID 86749409HCID 86749409, compound

Product 1

HCID 86749410HCID 86749410, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (E)-7-[4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinyl]-5-hydroxy-3-oxo-6-heptenoic acid, methyl ester (235 mg, 0.54 mmol) in THF (8 ml) was treated with triethylborane (1.0M in THF, 1.13 ml, 1.13 mmol). Twenty milliliters of air was bubbled through the solution and the mixture was stirred at room temperature for 25 minutes. The solution was cooled to -78° C. and treated with NaBH4 (20.7 mg, 0.55 mmol) followed by dropwise addition of dry methanol (1.25 ml). After stirring at -78° C. for 1.5 hours, the mixture was quenched with 30% H2O2 (3.5 ml) in H2O (8 ml). The mixture was kept at -78° C. for 15 minutes, then warmed to room temperature and stirred for 30 minutes. The solution was poured into 50% saturated NaHCO3 and extracted with Et 2 O (3×). The combined Et2O extracts were washed with H2O, saturated NaHCO3 and brine, then dried (Na2SO4), filtered and stripped. Purification of the resulting oil (Flash, Merck SiO2, 70% EtOAc/30% hexane) gave (3R*, 5S*, 6E)-7-[4-(4-fluorophenyl)-2-methyl-6-phenyl-3-pyridinyl]-3,5-dihydroxy-6-heptenoic acid, methyl ester (188 mg, 80%) as a colorless oily foam.

Workup

  1. customTwenty milliliters of air was bubbled through the solution
  2. temperatureThe solution was cooled to -78° C.
  3. stirringAfter stirring at -78° C. for 1.5 hours
  4. customthe mixture was quenched with 30% H2O2 (3.5 ml) in H2O (8 ml)
  5. waitThe mixture was kept at -78° C. for 15 minutes
  6. temperaturewarmed to room temperature
  7. stirringstirred for 30 minutes
  8. additionThe solution was poured into 50% saturated NaHCO3
  9. extractionextracted with Et 2 O (3×)
  10. washThe combined Et2O extracts were washed with H2O, saturated NaHCO3 and brine
  11. dry with materialdried (Na2SO4)
  12. filtrationfiltered
  13. customPurification of the resulting oil (Flash, Merck SiO2, 70% EtOAc/30% hexane)

Sources & evidence

ORD record
ord-a6a340c991dc4976817448dfbc5b220f
Source dataset
uspto-grants-1996_04
Patent number
US05506219

Reaction notes

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