تفاعل #70403

معادلة التفاعل

3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol

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3β-tert-butyldimethylsilyloxyandrostane-6,17-dione

المردود 75.0%

المذيبات

DMSO

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONwas added at room temperature
2. 2
   أخرىAfter 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL)
3. 3
   ترشيحAfter 15 min the mixture was filtered
4. 4
   غسيلthe cake was washed with H2O
5. 5
   استخلاصThe cake was extracted with Et2O (4×)
6. 6
   تجفيفThe combined organic extracts were dried over Na2SO4
7. 7
   أخرىevaporated to dryness

الإجراء التجريبي

To a stirred suspension of 3β-tert-butyldimethylsilyloxyandrostane-6α,17β-diol (EP 0825197 A2, 6.21 g) in DMSO (160 mL), IBX (16.45 g) was added at room temperature. After 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL). After 15 min the mixture was filtered and the cake was washed with H2O. The cake was extracted with Et2O (4×). The combined organic extracts were dried over Na2SO4 and evaporated to dryness to give 3β-tert-butyldimethylsilyloxyandrostane-6,17-dione (0.36 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 3.54 (1H, m), 2.47-1.08 (20H, m), 0.84 (9H, s), 0.77 (3H, s), 0.66 (1H, s), 0.01 (6H, s).

المصدر