Methanol → HCID 22810233, compound

HRID 1701230Notes

Reaction equation

HRID 1701230 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:31])[CH2:26][CH2:27][C:28]#[C:29][CH3:30])(=[O:5])[CH3:4].CO>O1CCCC1>[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:31])[CH2:26][CH2:27][C:28]#[C:29][CH3:30])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 22810263HCID 22810263, compound

Product 1

HCID 22810233HCID 22810233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At -40°, 420 mg. of sodium borohydride is added in incremental portions to a solution of 800 mg. of (1S,5R,6R,7R,3R)-7-acetoxy-6-[(E)-3-oxo-1-octen-6-ynyl]-3-(4-methoxycarbonyl-1-butyl)-2-oxabicyclo[3,3,0]octane in 24 ml. of methanol and 10 ml. of tetrahydrofuran. The mixture is agitated for 1 hour at -40°. Then the mixture is gently combined with 1 ml. of glacial acetic acid, concentrated under vacuum, the residue combined with methylene chloride, the organic extract shaken with 4% sodium bicarbonate solution, washed neutral with water, dried with magnesium sulfate, and evaporated under vacuum. After chromatography of the residue on silica gel with ether/pentane (6+4), 250 mg. of the corresponding compound in the β-configuration is obtained, along with 266 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 with 4% sodium bicarbonate solution
  5. washwashed neutral with water
  6. dry with materialdried with magnesium sulfate
  7. customevaporated under vacuum
  8. customof the corresponding compound in the β-configuration is obtained, along with 266 mg

Sources & evidence

ORD record
ord-235dbfff3f4243ef9c1620f447f900a6
Source dataset
uspto-grants-1980_03
Patent number
US04191694

Reaction notes

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