Water → HCID 70046759, compound

HRID 233642Notes

Reaction equation

HRID 233642 reaction equation
S(O[CH2:12][CH2:13][O:14][C@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C@H:17]([CH2:18][CH2:19][C@@H:20]3[C@@H:29]2[CH2:28][CH2:27][C@@:25]2([CH3:26])[C@:21]3([OH:39])[CH2:22][CH2:23][C@@H:24]2[C:34]2[CH:38]=[CH:37][O:36][CH:35]=2)[CH2:16]1)(C1C=CC(C)=CC=1)(=O)=O.[NH2:40][CH2:41][CH2:42][N:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1.O>C(O)C>[N:43]1([CH2:42][CH2:41][NH:40][CH2:12][CH2:13][O:14][C@H:15]2[CH2:32][CH2:31][C@@:30]3([CH3:33])[C@H:17]([CH2:18][CH2:19][C@@H:20]4[C@@H:29]3[CH2:28][CH2:27][C@@:25]3([CH3:26])[C@:21]4([OH:39])[CH2:22][CH2:23][C@@H:24]3[C:34]3[CH:38]=[CH:37][O:36][CH:35]=3)[CH2:16]2)[CH2:47][CH2:46][CH2:45][CH2:44]1

Participants

5

Reactant 3

HCID 962WaterHCID 13441-PyrrolidineethanamineHCID 86748784HCID 86748784, compound

Product 1

HCID 70046759HCID 70046759, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 0.20 g of 3β-(2-tosyloxyethoxy)-17β-(3-furyl)-5β-androstan-14β-ol in 2 ml of absolute ethanol 0.15 g of 1-(2-aminoethyl)pyrrolidine were added. The solution was kept at reflux under nitrogen for 3 hrs, then 10 ml of water were added. The residue was extracted with methylene chloride, the organic layer was washed with water to neutral pH, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude residue was purified by flash-chromatography (SiO2) using methylene chloride/methanol 95/5 as eluant to give 0.15 g of the title compound (I-ag).

Workup

  1. temperatureat reflux under nitrogen for 3 hrs
  2. extractionThe residue was extracted with methylene chloride
  3. washthe organic layer was washed with water to neutral pH
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated to dryness under reduced pressure
  6. customThe crude residue was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-026ec42c4489415184006bf6320a3b3c
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Reaction notes

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