Methanol → HCID 22810245, compound

HRID 1701232Notes

Reaction equation

HRID 1701232 reaction equation
[BH4-].[Na+].[C:3]([O:6][C@@H:7]1[CH2:14][C@H:13]2[C@H:9]([CH2:10][C@H:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:12]2)[C@H:8]1/[CH:23]=[CH:24]/[C:25](=[O:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])(=[O:5])[CH3:4].CO>C1COCC1>[C:3]([O:6][C@@H:7]1[CH2:14][C@H:13]2[C@H:9]([CH2:10][C@H:11]([CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])[O:12]2)[C@H:8]1/[CH:23]=[CH:24]/[C@@H:25]([OH:32])[CH2:26][CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 22810277HCID 22810277, compound

Product 1

HCID 22810245HCID 22810245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -40°, 230 mg. of sodium borohydride is added in incremental portions to a solution of 470 mg. of (1S,5R,6R,7R,3S)-7-acetoxy-6-[(1E)-7-methyl-3-oxo-1,6-octadienyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane in 14 ml. of methanol and 4 ml. of THF. The mixture is stirred for 1 hour at -40° and then combined with 0.6 ml. of glacial acetic acid, concentrated under vacuum, combined with methylene chloride, the organic extract shaken in 4% sodium bicarbonate solution, washed neutral with water, dried over magnesium sulfate, and evaporated under vacuum. After separation by chromatography on silica gel, ether/pentane (1+1) yields 120 mg. of the corresponding β-configured compound and 160 mg. of the title compound as a colorless oil.

Workup

  1. customAt -40°
  2. concentrationof glacial acetic acid, concentrated under vacuum
  3. extractionthe organic extract
  4. stirringshaken in 4% sodium bicarbonate solution
  5. washwashed neutral with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under vacuum
  8. customAfter separation by chromatography on silica gel, ether/pentane (1+1)
  9. customyields 120 mg

Sources & evidence

ORD record
ord-12c2503447aa437998d1e744b53d4d0d
Source dataset
uspto-grants-1980_03
Patent number
US04191694

Reaction notes

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