ethyl (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxylate → (E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol

HRID 725261노트

반응식

HRID 725261 반응식
[OH:1][C@H:2]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:23]2[CH2:22][CH2:21][C@@:20]2([CH3:28])[C@:8]3([OH:29])[CH2:9][CH2:10][C@@H:11]2/[CH:12]=[C:13](\[CH3:19])/[C:14](OCC)=[O:15])[CH2:3]1>O1CCCC1.[AlH](CC(C)C)CC(C)C.CCCCCC>[OH:15][CH2:14]/[C:13](/[CH3:19])=[CH:12]/[C@@H:11]1[C@:20]2([CH3:28])[C@@:8]([OH:29])([C@H:7]3[C@H:23]([CH2:22][CH2:21]2)[C@:24]2([CH3:27])[C@@H:4]([CH2:3][C@@H:2]([OH:1])[CH2:26][CH2:25]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1

참가 물질

5

반응물 1

HCID 86751868ethyl (E)-3beta,14beta-dihydroxy-21-methyl-5beta-pregn-20-ene-21-carboxylate

생성물 1

HCID 10690052(E)-21-hydroxymethyl-21-methyl-5beta-pregn-20-ene-3beta,14beta-diol수율 96.5%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 14487Diisobutylaluminum hydride용매

실험 절차

To a solution of 9.60 g of ethyl (E)-3β,14β-dihydroxy-21-methyl-5β-pregn-20-ene-21-carboxylate (Boutagy J. and Thomas R., Aust. J. Pharm, Chem., 1972, NS1, 67) in 370 ml of dry tetrahydrofuran, 104 ml of 1M i-Bu2AlH in hexane were added dropwise under nitrogen at -78° C. After 2 hrs the reaction was quenched with a solution of 46.0 g of sodium sulfate in 350 ml of water and stirred at room temperature for 2 hours. The mixture was then filtered through Celite and washed with methylene chloride. The organic layer was separated, dried over anhydrous sodium sulfate and evaporated to dryness to give 8.30 g of (E)-21-hydroxymethyl-21-methyl-5β-pregn-20-ene-3β,14β-diol as an off-white solid.

후처리

  1. customAfter 2 hrs the reaction was quenched with a solution of 46.0 g of sodium sulfate in 350 ml of water
  2. filtrationThe mixture was then filtered through Celite
  3. washwashed with methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-bfbd5c13ea4c4713b66cb7dd519caec8
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705662

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