Water → 3beta-(2-(N-(2-(1-Pyrrolidinyl)ethyl)methylamino)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol

HRID 1647638노트

반응식

HRID 1647638 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 700460273beta-(2-(N-(2-(1-Pyrrolidinyl)ethyl)methylamino)ethylthio)-17beta-(3-furyl)-5beta-androstan-14beta-ol수율 60.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-509622baa2334647a31641295bd5bfbd
출처 데이터셋
uspto-grants-1995_07
특허 번호
US05432169

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