3beta-Tert-butyldimethylsilyloxyandrostane-6,17-dione → 3beta-Hydroxy-5alpha-androstan-6,17-dione

HRID 1912729노트

반응식

HRID 1912729 반응식
[Si]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:11]([C:12](=[O:29])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1)(C(C)(C)C)(C)C>CCO.Cl>[OH:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:11]([C:12](=[O:29])[CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C:18]2=[O:28])[CH2:10]1

참가 물질

4

반응물 1

HCID 690112643beta-Tert-butyldimethylsilyloxyandrostane-6,17-dione

생성물 1

HCID 690126423beta-Hydroxy-5alpha-androstan-6,17-dione수율 86%

시약·촉매·용매 2

HCID 313Hydrochloric Acid용매HCID 702Ethanol용매

실험 절차

To a stirred suspension of 3β-tert-butyldimethylsilyloxyandrostane-6,17-dione (2.00 g) in EtOH (20 mL), 37% HCl (40 μL) was added. After 3 h the solution was quenched with 5% aqueous NaHCO3 to pH 7. The organic solvent was evaporated and the aqueous phase was extracted with CH2Cl2 (4×350 mL). The combined organic extracts were washed with saturated aqueous NH4Cl, brine, H2O, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 90/10) to give 3β-hydroxyandrostane-6,17-dione (1.25 g, 86%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 4.56 (d, 1H), 3.31 (m, 1H), 2.45-1.15 (m, 20H), 0.77 (s, 3H), 0.65 (s, 3H).

후처리

  1. additionwas added
  2. customAfter 3 h the solution was quenched with 5% aqueous NaHCO3 to pH 7
  3. customThe organic solvent was evaporated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (4×350 mL)
  5. washThe combined organic extracts were washed with saturated aqueous NH4Cl, brine, H2O
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customThe residue was purified by flash chromatography (SiO2, cyclohexane/EtOAc 90/10)

출처 및 근거

ORD 기록
ord-9ba2e4d2c48d449caaf4c6a34de789cd
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609644B2

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