Toluene → HCID 69828311, compound

HRID 2227242Notes

Reaction equation

HRID 2227242 reaction equation
[Si](Cl)(C(C)(C)C)(C)[CH3:2].[CH3:9][C:10]([Si:13]([CH3:36])([CH3:35])[O:14][C@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C:17](=[CH:18][CH2:19][C@@H:20]3[C@@H:29]2[CH2:28][CH2:27][C@@:25]2([CH3:26])[C@H:21]3[CH:22]=[CH:23][C:24]2=[O:34])[CH2:16]1)([CH3:12])[CH3:11].C[Al](C)C.C1(C)C=CC=CC=1.C[Si](Cl)(C)C>CN(C=O)C.O1CCCC1.O>[CH3:12][C:10]([Si:13]([CH3:36])([CH3:35])[O:14][C@H:15]1[CH2:32][CH2:31][C@@:30]2([CH3:33])[C:17](=[CH:18][CH2:19][C@@H:20]3[C@@H:29]2[CH2:28][CH2:27][C@@:25]2([CH3:26])[C@H:21]3[C@@H:22]([CH3:2])[CH2:23][C:24]2=[O:34])[CH2:16]1)([CH3:9])[CH3:11]

Participants

9

Reactant 5

HCID 1140TolueneHCID 6397ChlorotrimethylsilaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 12149919HCID 12149919, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 69828311HCID 69828311, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepare M82 by treating a solution of M81 in DMF with t-butyldimethylsilyl chloride following the procedure described in example 13a. To a solution of 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]androst-5,15-dien-17-one (M82) (10.0 g, 24.96 mmol) and cuprous bromide (71.5 mg, 0.5 mmol) dissolved in tetrahydrofuran (100 mL) under a nitrogen atmosphere, add a 2M solution of tri-methylaluminum in toluene (13.8 mL, 27.6 mmol). Add trimethylsilyl chloride (5.88 g, 54 mmol) dropwise to the solution. After 2 hours, add water (5 mL) cautiously. Remove the solids by filtration and wash. Purify the crude product by flash chromatography to give 3β-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-15α-methylandrost-5-en-17-one (N88a).

Workup

  1. customPrepare M82
  2. customRemove the solids
  3. filtrationby filtration
  4. washwash
  5. customPurify the crude product by flash chromatography

Sources & evidence

ORD record
ord-f5841f27c5e3445ebc0258e7125a4cdf
Source dataset
uspto-grants-2002_07
Patent number
US06413951B2

Reaction notes

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