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 725261ノート

反応式

HRID 725261 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 14487Diisobutylaluminum hydride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bfbd5c13ea4c4713b66cb7dd519caec8
出典データセット
uspto-grants-1998_01
特許番号
US05705662

反応ノート

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