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

HRID 333683

반응식

HRID 333683 반응식
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

참가 물질

5

반응물 2

HCID 4304157Potassium;tri(butan-2-yl)boranuide2회HCID 66657133Androstane-3,11,17-trione

생성물 1

HCID 219687643beta-Hydroxy-androstane-11,17-dione수율 99.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-bc71fd852b374fd485a3d579acfd6eb9
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883770B2

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