(1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-ol → HCID 178421246, compound

HRID 725173Notes

Reaction equation

HRID 725173 reaction equation
[CH:1]([C@@H:3]1[C@:11]2([CH3:12])[C@@:6]([OH:19])([CH2:7][C@@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)[CH2:5][CH2:4]1)=O.C(=O)(O)O.[NH2:24][NH:25][C:26]([NH2:28])=[NH:27]>Cl.O1CCOCC1>[NH:25](/[N:24]=[CH:1]/[C@@H:3]1[C@:11]2([CH3:12])[C@@:6]([OH:19])([CH2:7][C@@H:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:9][CH2:10]2)[CH2:5][CH2:4]1)[C:26]([NH2:28])=[NH:27]

Participants

5

Reactant 2

HCID 11054353(1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-olHCID 178513185HCID 178513185, compound

Product 1

HCID 178421246HCID 178421246, compoundYield 69.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 0.57 g of (1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-ol and 1.50 g of aminoguanidine hydrogencarbonate in 30 ml of 0.01N hydrochloric acid and 80 ml of dioxane was kept at room temperature for 3 days and then evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 78/20/2 as the eluant. The fractions containing the title compound were collected and evaporated to dryness. The residue was triturated with ethanol/ethyl acetate to give 0.48 g of the title compound (I-aa) as a white solid.

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe crude product was purified by flash-chromatography (SiO2)
  3. additionThe fractions containing the title compound
  4. customwere collected
  5. customevaporated to dryness
  6. customThe residue was triturated with ethanol/ethyl acetate

Sources & evidence

ORD record
ord-1b219ce186db4c9fb50e4966f296d2de
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

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