2-Hydrazino-delta-2-imidazoline hydrobromide → (3S,5R,8R,9S,10S,13R,14S,17S)-17-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diol

HRID 1735735Notes

Reaction equation

HRID 1735735 reaction equation
Br.[NH:2]([C:4]1[NH:5][CH2:6][CH2:7][N:8]=1)[NH2:3].[OH:9][C@H:10]1[CH2:27][CH2:26][C@@:25]2([CH3:28])[C@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:24]2[CH2:23][CH2:22][C@@:20]2([CH3:21])[C@:16]3([OH:31])[CH2:17][CH2:18][C@@H:19]2[CH:29]=O)[CH2:11]1>O.O1CCOCC1>[NH:8]1[CH2:7][CH2:6][N:5]=[C:4]1[NH:2]/[N:3]=[CH:29]/[C@H:19]1[CH2:18][CH2:17][C@:16]2([OH:31])[C@H:15]3[C@H:24]([CH2:23][CH2:22][C@:20]12[CH3:21])[C@:25]1([CH3:28])[C@@H:12]([CH2:11][C@@H:10]([OH:9])[CH2:27][CH2:26]1)[CH2:13][CH2:14]3

Participants

5

Reactant 2

HCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 109033043beta,14beta-Dihydroxy-5beta-androstane-17beta-carboxaldehyde

Product 1

HCID 10834968(3S,5R,8R,9S,10S,13R,14S,17S)-17-[(E)-(4,5-dihydro-1H-imidazol-2-ylhydrazinylidene)methyl]-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-3,14-diolYield 43.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 0.93 g of 2-hydrazino-2-imidazoline hydrobromide in 45 ml of water and 30 ml of dioxane a solution of 1.10 g of 3β,14β-dihydroxy-5β-androstane-17β-carboxaldehyde (Boutagy J. and Thomas R., Aust. J. Chem., 1971, 24, 2723) in 30 ml of dioxane was added dropwise at room temperature. After 2 hrs, the solution was evaporated to dryness under reduced pressure. The crude product was crystallized from ethanol/water and then from ethanol to give 0.60 g of the title compound (I-aa) as hydrobromide, white solid.

Workup

  1. customthe solution was evaporated to dryness under reduced pressure
  2. customThe crude product was crystallized from ethanol/water

Sources & evidence

ORD record
ord-34fad7ad5f6f4382b5ae8f5f093bd4b3
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

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