Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylate → HCID 14801334、化合物

HRID 1165504

反応式

HRID 1165504 の反応式
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C@:8]12[CH2:25][CH2:24][C@H:23]3[C@@H:13]([CH2:14][CH2:15][C:16]4[C@:21]3([CH3:22])[CH2:20][CH2:19][C:18](=[O:26])[CH:17]=4)[C@@H:12]1[CH2:11][CH2:10][C@@H:9]2[C:27](OC)=[O:28]>C1COCC1>[OH:28][CH2:27][C@H:9]1[CH2:10][CH2:11][C@H:12]2[C@H:13]3[C@H:23]([CH2:24][CH2:25][C@:8]12[CH3:7])[C@:21]1([CH3:22])[C:16](=[CH:17][CH:18]([OH:26])[CH2:19][CH2:20]1)[CH2:15][CH2:14]3

参加物

4

反応物 2

HCID 165014Methyl (17beta)-3-oxoandrost-4-ene-17-carboxylateHCID 21226445Aluminium lithium hydride3 回

生成物 1

HCID 14801334HCID 14801334、化合物収率 103.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

Approximately 750 ml of dry THF was added to a 3-neck round bottom flask equipped with a condenser, argon bubbler and mechanical stirrer. The flask was cooled to 0° C. and lithium aluminum hydride (LAH) (11.39 g, 0.3 mol) was slowly added. After all of the LAH was added, the flask was warmed to room temperature. A solution of methyl androst-4-ene-3-one-17β-carboxylate (66 g, 0.2 mol) in 600 ml of THF was very slowly added to the LAH slurry. After the addition of the steroid, the reaction mixture was slowly warmed to reflux. After 2 hours the excess LAH was quenched with 11.4 ml water, 11.4 ml 15% sodium hydroxide (NaOH) and 28 ml water. The salts were removed by filtration and washed with approximately 1 liter of warm THF. Concentration of the combined organic solutions afforded 63 g (94%) of 17β-(hydroxymethyl)-androst-4-ene-3-ol as mixture of α and β isomers.

後処理

  1. customequipped with a condenser
  2. temperaturethe flask was warmed to room temperature
  3. temperaturethe reaction mixture was slowly warmed to reflux
  4. customAfter 2 hours the excess LAH was quenched with 11.4 ml water, 11.4 ml 15% sodium hydroxide (NaOH) and 28 ml water
  5. customThe salts were removed by filtration
  6. washwashed with approximately 1 liter of warm THF

出典と根拠

ORDレコード
ord-b2c69886ef72425189c760524cc0a1c8
出典データセット
uspto-grants-1990_03
特許番号
US04910226

関連ノート

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