Water → HCID 70046027, compound

HRID 233649

Reaction equation

HRID 233649 reaction equation
[N:1]1([CH2:6][CH2:7][NH:8][CH3:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].S(O[CH2:23][CH2:24][S:25][C@H:26]1[CH2:43][CH2:42][C@@:41]2([CH3:44])[C@H:28]([CH2:29][CH2:30][C@@H:31]3[C@@H:40]2[CH2:39][CH2:38][C@@:36]2([CH3:37])[C@:32]3([OH:50])[CH2:33][CH2:34][C@@H:35]2[C:45]2[CH:49]=[CH:48][O:47][CH:46]=2)[CH2:27]1)(C1C=CC(C)=CC=1)(=O)=O.O>CN(C)C=O>[N:1]1([CH2:6][CH2:7][N:8]([CH3:9])[CH2:23][CH2:24][S:25][C@H:26]2[CH2:43][CH2:42][C@@:41]3([CH3:44])[C@H:28]([CH2:29][CH2:30][C@@H:31]4[C@@H:40]3[CH2:39][CH2:38][C@@:36]3([CH3:37])[C@:32]4([OH:50])[CH2:33][CH2:34][C@@H:35]3[C:45]3[CH:49]=[CH:48][O:47][CH:46]=3)[CH2:27]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 295976Methyl(2-(pyrrolidin-1-yl)ethyl)amineHCID 867487853beta-(2-Tosyioxyethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

Product 1

HCID 70046027HCID 70046027, compoundYield 60.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.34 g of N-(2-(1-pyrrolidinyl)ethyl)methylamine in 5 ml of dimethylformamide, 0.045 g of NaH (60% dispersion in mineral oil) were added under nitrogen and the mixture was stirred at room temperature for half an hr; a solution of 0.50 g of 3β-(2-tosyloxyethylthio)-17β-(3-furyl)-5β-androstan-14β-ol, prepared as described in Ex. 51, in 2 ml of dimethylformamide was added, the mixture was stirred for another 4 hrs and then 7 ml of water were poured in. The residue was extracted with ethyl acetate, the organic solution was washed with water to neutral pH, dried over anhydrous sodium sulfate and evaporated to dryness under reduced pressure. The crude product was purified by flash-chromatography (SiO2) using methylene chloride/methanol 95/5 as eluant to give 0.28 g of the title compound (I-ca) as an amorphous solid.

Workup

  1. stirringthe mixture was stirred for another 4 hrs
  2. extractionThe residue was extracted with ethyl acetate
  3. washthe organic solution 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 product was purified by flash-chromatography (SiO2)

Sources & evidence

ORD record
ord-02c04493e8584137a08185b56d60bf2e
Source dataset
uspto-grants-1997_01
Patent number
US05593982

Linked notes

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