HCID 69008529, compound → 3beta-Tert-butyldimethylsilyloxyandrostane-6,17-dione

HRID 1912728Notes

Reaction equation

HRID 1912728 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[CH:11]([C@@H:12]([OH: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@@H:18]2[OH:28])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CS(C)=O>[Si:1]([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:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 69008529HCID 69008529, compound

Product 1

HCID 690112643beta-Tert-butyldimethylsilyloxyandrostane-6,17-dioneYield 75%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

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-butyldimethylsilyloxy-androstane-6,17-dione (0.36 g, 75%). 1H-NMR (300 MHz, DMSO-d6, ppm from TMS: δ 3.54 (m, 1H), 2.47-1.08 (m, 20H), 0.84 (s, 9H), 0.77 (s, 3H), 0.66 (s, 1H), 0.01 (s, 6H).

Workup

  1. additionwas added at room temperature
  2. customAfter 1.5 h the mixture was quenched at room temperature by addition of H2O (300 mL)
  3. filtrationAfter 15 min the mixture was filtered
  4. washthe cake was washed with H2O
  5. extractionThe cake was extracted with Et2O (4×)
  6. dry with materialThe combined organic extracts were dried over Na2SO4
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-109cf980935748f4beba7f683ffe291f
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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