Sodium borohydride → (1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-nonene-6-ynyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octane-3-one

HRID 1902667Notes

Reaction equation

HRID 1902667 reaction equation
[BH4-].[Na+].[O:3]=[C:4]([CH:25]([CH3:31])[CH2:26][C:27]#[C:28][CH2:29][CH3:30])/[CH:5]=[CH:6]/[C@H:7]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][C:10](=[O:24])[O:11]2>CO.CCOCC>[OH:3][C@@H:4]([CH:25]([CH3:31])[CH2:26][C:27]#[C:28][CH2:29][CH3:30])/[CH:5]=[CH:6]/[C@H:7]1[C@H:14]([O:15][C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH2:13][C@H:12]2[C@@H:8]1[CH2:9][C:10](=[O:24])[O:11]2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 13472481(1S,5R,6R,7R)-7-Benzoyloxy-6-[(E)-(4RS)-4-methyl-3-oxonon-1-en-6-inyl]-2-oxabicyclo[3,3,0]octan-3-one

Product 1

HCID 13472483(1S,5R,6R,7R)-6-[(E)-(3S,4RS)-3-hydroxy-4-methyl-1-nonene-6-ynyl]-7-benzoyloxy-2-oxabicyclo[3.3.0]octane-3-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
-40 °C

Procedure

3.4 of sodium borohydride is added batchwise to a solution of 6 g of the ketone prepared in example (6e) in 200 ml of methanol, at -40° C., and the mixture is stirred for 1 h at -40° C. under argon. Next it is diluted with ether, washed with water until neutral, dried over magnesium sulfate and vacuum evaporated. By means of column chromatography on silcia gel using ether/hexane (8/2), first 2.6 g of the title compound (3-alpha-hydroxy) is elutriated, next, as the more polar component, 1.9 g of the corresponding isomeric 3 beta-hydroxy compound.

Workup

  1. washwashed with water until neutral,
  2. dry with materialdried over magnesium sulfate and vacuum
  3. customevaporated

Sources & evidence

ORD record
ord-7e49187b9e884bf9a1ba2d694c18f670
Source dataset
uspto-grants-1982_12
Patent number
US04364950

Reaction notes

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