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

HRID 2275462Notes

Reaction equation

HRID 2275462 reaction equation
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

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2aa24e6b39204f42b93a056f0041d89d
Source dataset
uspto-grants-2015_09
Patent number
US09127036B2

Reaction notes

Loading…