Hydrochloric Acid → (1S,3aS,5S,7aR)-1-[(E)-2-aminoethoxyiminomethyl]-7a-methyl-5-phenyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-ol

HRID 725175Notes

Reaction equation

HRID 725175 reaction equation
Cl.Cl.[NH2:3][CH2:4][CH2:5][O:6][NH2:7].C([O-])(=O)C.[Na+].Cl.[CH:14]([C@@H:16]1[C@:24]2([CH3:25])[C@@:19]([OH:32])([CH2:20][C@@H:21]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:22][CH2:23]2)[CH2:18][CH2:17]1)=O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O>[NH2:3][CH2:4][CH2:5][O:6]/[N:7]=[CH:14]/[C@@H:16]1[C@:24]2([CH3:25])[C@@:19]([OH:32])([CH2:20][C@@H:21]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:22][CH2:23]2)[CH2:18][CH2:17]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 517045Sodium AcetateHCID 11054353(1S,3aS,5S,7aR)-1-formyl-5-phenyl-7a-methylperhydroinden-3a-olHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

Product 1

HCID 10958069(1S,3aS,5S,7aR)-1-[(E)-2-aminoethoxyiminomethyl]-7a-methyl-5-phenyl-2,3,4,5,6,7-hexahydro-1H-inden-3a-olYield 69.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 6.30 g of 0.12 g of 2-aminoethoxyamine dihydrochloride, 0.28 g of sodium acetate in 2 ml of dioxane and 1 ml of water was made aid to pH 4.5 with 3N HCl. A solution of 0.20 g of (1S,3aS,5S,7aR)-1-formyl-5-phenyl -7a-methylperhydroinden-3a-ol in 1 ml of dioxane and 0.5 ml of water was added dropwise at room temperature. After 1 hr the solution was alkalinized with 10% aqueous Na2CO3 and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The crude product was ground with diethyl ether to give 0.17 g of the title compound (I-am) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-0ed5ac84fe694c92b3957fa6fcc6899b
Source dataset
uspto-grants-1998_01
Patent number
US05705531

Reaction notes

Loading…