Sodium Acetate → [(5R,8R,9S,10S,13R,14S,17S)-17-[(E)-2-(dimethylamino)ethoxyiminomethyl]-10,13-dimethyl-3-oxo-2,4,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-14-yl] acetate

HRID 1757087Notes

Reaction equation

HRID 1757087 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:9])[CH2:5][CH2:6][O:7][NH2:8].[C:10]([O-:13])(=[O:12])[CH3:11].[Na+].[O:15]=[C:16]1[CH2:33][CH2:32][C@@:31]2([CH3:34])[C@H:18]([CH2:19][CH2:20][C@@H:21]3[C@@H:30]2[CH2:29][CH2:28][C@@:26]2([CH3:27])[C@:22]3(O)[CH2:23][CH2:24][C@@H:25]2[CH:35]=O)[CH2:17]1>C(O)(=O)C.O1CCOCC1>[C:10]([O:13][C@@:22]12[C@H:21]3[C@@H:30]([C@:31]4([CH3:34])[C@H:18]([CH2:19][CH2:20]3)[CH2:17][C:16](=[O:15])[CH2:33][CH2:32]4)[CH2:29][CH2:28][C@:26]1([CH3:27])[C@@H:25](/[CH:35]=[N:8]/[O:7][CH2:6][CH2:5][N:4]([CH3:9])[CH3:3])[CH2:24][CH2:23]2)(=[O:12])[CH3:11]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 10176354O-[2-(dimethylamino)ethyl]hydroxylamine dihydrochlorideHCID 86748908HCID 86748908, compound

Product 1

HCID 88123149[(5R,8R,9S,10S,13R,14S,17S)-17-[(E)-2-(dimethylamino)ethoxyiminomethyl]-10,13-dimethyl-3-oxo-2,4,5,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-14-yl] acetateYield 78.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.21 g of 2-dimethylaminoethoxyamine dihydrochloride, 2.00 g of sodium acetate in 25 ml of 0.2M acetic acid a solution of 0.30 g of 3-oxo-14β-hydroxy-5β-androstane-17β-carboxaldehyde (Prepn. 6) in 40 ml of dioxane was added dropwise. After 2 hrs at room temperature, the mixture was evaporated to dryness under reduced pressure and the crude product was extracted three times with iso-propanol. Evaporation of the solvent gave 0.33 g of (E)-3-oxo-17β-(2-dimethylaminoethoxyiminomethyl)-5β-androstane-14β-ol acetate as a white foam.

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. extractionthe crude product was extracted three times with iso-propanol
  3. customEvaporation of the solvent

Sources & evidence

ORD record
ord-de0c832f9ba2442aa3c3b7f9f3976dfd
Source dataset
uspto-grants-1995_08
Patent number
US05444055

Reaction notes

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