Triethylamine → HCID 88124883, compound

HRID 1735741Notes

Reaction equation

HRID 1735741 reaction equation
[OH:1][C@H:2]1[CH2:19][CH2:18][C@@:17]2([CH3:20])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[CH2:15][CH2:14][C@@:12]2([CH3:13])[C@:8]3([OH:22])[CH2:9][CH2:10][C:11]2=O)[CH2:3]1.Br.[NH:24]([C:26]1[NH:27][CH2:28][CH2:29][N:30]=1)[NH2:25].C(N(CC)CC)C.[OH-].[Na+]>C(O)C.O>[NH:30]1[CH2:29][CH2:28][N:27]=[C:26]1[NH:24]/[N:25]=[C:11]1/[C@:12]2([CH2:14][CH2:15][C@H:16]3[C@@H:7]([CH2:6][CH2:5][C@H:4]4[C@:17]3([CH3:20])[CH2:18][CH2:19][C@H:2]([OH:1])[CH2:3]4)[C@@:8]2([OH:22])[CH2:9][CH2:10]/1)[CH3:13]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromideHCID 131173483beta,14beta-Dihydroxy-5beta-androstane-17-one

Product 1

HCID 88124883HCID 88124883, compoundYield 56.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.60 g of 3β,14β-dihydroxy-5β-androstane-17-one (Lindig C., J. Prakt. Chem., 1983, 325, 587), 1.00 g of 2-hydrazino-2-imidazoline hydrobromide and 1.50 ml of triethylamine in 50 ml of ethanol and 50 mI of water was stirred at reflux for 2 days. After cooling the mixture was added with 1N sodium hydroxide until pH 12.5 was reached. The mixture was evaporated under reduced pressure and the residue was purified by flash-chromatography (SiO2) using chloroform/methanol/28% ammonium hydroxide 88/20/2 as eluant; the fractions containing the title compound were collected and evaporated to dryness. The residue was ground with ethanol/diethyl ether to give 0.43 g of the title compound (I-bo) as a white solid.

Workup

  1. temperatureat reflux for 2 days
  2. temperatureAfter cooling the mixture
  3. customThe mixture was evaporated under reduced pressure
  4. customthe residue was purified by flash-chromatography (SiO2)
  5. additionthe fractions containing the title compound
  6. customwere collected
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-c3237d3e139d4599be705e5abd04790b
Source dataset
uspto-grants-1996_07
Patent number
US05538960

Reaction notes

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