Pyridine → 19-t-Butyldimethylsiloxy-4-androstene-3,17-dione

HRID 371826

반응식

HRID 371826 반응식
[OH:1][CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].N1C=CC=CC=1>CN(C)C=O>[O:1]([CH2:2][C@@:3]12[C@@H:20]3[C@H:11]([C@H:12]4[C@@:16]([CH2:18][CH2:19]3)([CH3:17])[C:15](=[O:21])[CH2:14][CH2:13]4)[CH2:10][CH2:9][C:8]1=[CH:7][C:6](=[O:22])[CH2:5][CH2:4]2)[Si:23]([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 25237919-Hydroxyandrostenedione

생성물 1

HCID 1057397419-t-Butyldimethylsiloxy-4-androstene-3,17-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

19-Hydroxy-4-androstene-3,17-dione, t-butyldimethylsilylchloride and pyridine are mixed in dry dimethylformamide and heated on a steam bath overnight. The reaction mixture is poured onto water and stirred well for 15 minutes. The resulting solid is filtered and dissolved in methylenechloride, dried over magnesium sulfate and the solvent removed. The residue is crystallized from an acetone-hexane solution to yield 19-t-butyldimethylsiloxy-4-androstene-3,17-dione.

후처리

  1. temperatureheated on a steam bath overnight
  2. additionThe reaction mixture is poured onto water
  3. filtrationThe resulting solid is filtered
  4. dissolutiondissolved in methylenechloride
  5. dry with materialdried over magnesium sulfate
  6. customthe solvent removed
  7. customThe residue is crystallized from an acetone-hexane solution

출처 및 근거

ORD 기록
ord-0d06e6505c2c4bc38a1a215cd98f8202
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04087524

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