Potassium;tri(butan-2-yl)boranuide → 3beta-Hydroxy-androstane-11,17-dione
Reaction equation
C([BH-](C(CC)C)C(CC)C)(CC)C.[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]1Participants
5
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
- customThe reaction mixture is quenched with aqueous NaOH solution (2M, 70 mL)
- customThe crude reaction mixture
- washthe organic layer is washed with water (3×75 mL), saturated brine solution (100 mL)
- dry with materialdried over MgSO4 (75 g)
- customThe solvent is removed under vacuum
Sources & evidence
- ORD record
- ord-966e97574c67452094f46ddf5a122c8c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09050349B2
Reaction notes
Loading…