HCID 70521224, compound → HCID 56630809, compound

HRID 1249476Notes

Reaction equation

HRID 1249476 reaction equation
[OH:1][CH:2]1[CH2:10][CH2:9][CH2:8][C:7]2([CH3:11])[CH:3]1[CH2:4][CH2:5][CH:6]2[CH:12]([CH3:22])[CH2:13][CH:14]1[O:18][C:17](=[O:19])[C:16]([OH:21])([CH3:20])[CH2:15]1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1C1C=CC=C[NH+]=1.[Cr](Cl)([O-])(=O)=O>C(O)(C)C.C(Cl)Cl>[CH3:11][C:7]12[CH:6]([CH:12]([CH3:22])[CH2:13][CH:14]3[O:18][C:17](=[O:19])[C:16]([OH:21])([CH3:20])[CH2:15]3)[CH2:5][CH2:4][CH:3]1[C:2](=[O:1])[CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 2

HCID 70521224HCID 70521224, compoundHCID 178526115HCID 178526115, compound

Product 1

HCID 56630809HCID 56630809, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 90.0 mg (0.290 mmol) of [3R-[3 beta,5S,(5beta,(R*)-1R*-(1 beta,3a alpha,4alpha,7a beta)]]-dihydro-5-[2-(octahydro-4-hydroxy-7a-methyl-1H-inden-1-yl)-2-methylethyl]-3-hydroxy-3-methyl-2(3H)-furanone in 4 ml. of dry methylene chloride was treated at room temperature with 340.0 mg (1.162 mmol) of 2,2'-bipyridinium chlorochromate for 5.5 hours. A few drops of isopropyl alcohol were then added and the resulting mixture diluted with 50 ml of methylene chloride, filtered through Celite® filter aid. After evaporation of the solvent, the residue was dissolved in 100 ml. of ethyl acetate, extracted with 3×20 ml. of 1N hydrochloric acid and then with 3×30 ml of brine. The organic phases were combined, dried and evaporated to give 89.0 mg (quantitative yield) of [3R-[3 beta,5S,(5 beta,(R*)-1R*-(1 beta,3a alpha,7a beta)]]-dihydro-5-[2-(octahydro-7a-methyl-1H-inden-4-one-1-yl)-2-methylethyl]-3-hydroxy-3-methyl-2(3H)-furanone.

Workup

  1. filtrationfiltered through Celite®
  2. filtrationfilter aid
  3. customAfter evaporation of the solvent
  4. dissolutionthe residue was dissolved in 100 ml
  5. extractionof ethyl acetate, extracted with 3×20 ml
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-6bde70002db145a0ab1d2a41724290d4
Source dataset
uspto-grants-1986_12
Patent number
US04632784

Reaction notes

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