Potassium;tri(butan-2-yl)boranuide → 3beta-Hydroxy-androstane-11,17-dione

HRID 1034931ノート

反応式

HRID 1034931 の反応式
CCC(C)[BH-](C(C)CC)C(C)CC.[K+].[CH3:15][C@:16]12[CH2:33][C:32](=[O:34])[C@H:31]3[C@@H:21]([CH2:22][CH2:23][CH:24]4[C@:29]3([CH3:30])[CH2:28][CH2:27][C:26](=[O:35])[CH2:25]4)[C@@H:20]1[CH2:19][CH2:18][C:17]2=[O:36]>C1COCC1.C(OCC)(=O)C>[OH:35][C@H:26]1[CH2:27][CH2:28][C@@:29]2([CH3:30])[CH:24]([CH2:23][CH2:22][C@@H:21]3[C@@H:31]2[C:32](=[O:34])[CH2:33][C@@:16]2([CH3:15])[C@H:20]3[CH2:19][CH2:18][C:17]2=[O:36])[CH2:25]1

参加物

5

反応物 2

HCID 4304157Potassium;tri(butan-2-yl)boranuide2 回HCID 66657133Androstane-3,11,17-trione

生成物 1

HCID 219687643beta-Hydroxy-androstane-11,17-dione収率 99.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
-78 °C

実験手順

K-SELECTRIDE® (potassium tri-sec-butylborohydride, 98.39 mL, 98.01 mmol, 1M solution in THF) is added to a solution of Compound 1.13 (33.0 g, 109.27 mmol) in THF (330 mL) over 15 minutes under an inert atmosphere at −78° C. and is stirred for about 3-4 h at −78° C. The reaction mixture is quenched with aqueous NaOH solution (2M, 70 mL). The crude reaction mixture is diluted with ethyl acetate (500 mL) and the organic layer is washed with water (3×75 mL), saturated brine solution (100 mL) and dried over MgSO4 (75 g). The solvent is removed under vacuum to afford 33 g of crude material. The crude product is subjected to acetylation without purification.

後処理

  1. customThe reaction mixture is quenched with aqueous NaOH solution (2M, 70 mL)
  2. customThe crude reaction mixture
  3. washthe organic layer is washed with water (3×75 mL), saturated brine solution (100 mL)
  4. dry with materialdried over MgSO4 (75 g)
  5. customThe solvent is removed under vacuum

出典と根拠

ORDレコード
ord-d93e7fcac8934079bc3fc347315de9f2
出典データセット
uspto-grants-2013_10
特許番号
US08546367B2

反応ノート

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