Hydrofluoric Acid → HCID 22875678, compound

HRID 362800Notes

Reaction equation

HRID 362800 reaction equation
[Si]([O:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C@H:18]([NH:19][CH2:20][CH2:21][CH2:22]2)[CH2:17][C@@H:16]3[CH3:30])[CH2:13][CH2:12]1)[CH3:10])(C(C)(C)C)(C)C.F.C(=O)(O)[O-:33].[Na+]>C(#N)C>[OH:8][CH:9]([C@@H:11]1[C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C@H:25]([CH2:26][CH2:27]2)[C@:23]2([CH3:24])[C@H:18]([NH:19][C:20](=[O:33])[CH2:21][CH2:22]2)[CH2:17][C@@H:16]3[CH3:30])[CH2:13][CH2:12]1)[CH3:10]

Participants

5

Reactant 3

HCID 14917Hydrofluoric AcidHCID 516892Sodium BicarbonateHCID 22875680HCID 22875680, compound2×

Product 1

HCID 22875678HCID 22875678, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a slurry of crude 20-tert-butyldimethylsilyloxy-7β-methyl-5α-4-azapregnane (25.2 g, product of Step 9) in acetonitrile (300 mL) was added an aqueous solution of hydrofluoric acid (12 mL). After stirring for 8 hr at room temperature, the reaction mixture was cooled to 0° C. and saturated sodium bicarbonate solution was slowly added. The mixture was extracted with methylene chloride (3×500 mL) and the combined extracts washed with water, saturated salt solution and dried over anhydrous sodium sulfate. The solvent was removed by rotoevaporation to give the title compound which was used without purification in the subsequent reaction.

Workup

  1. temperaturethe reaction mixture was cooled to 0° C.
  2. extractionThe mixture was extracted with methylene chloride (3×500 mL)
  3. washthe combined extracts washed with water, saturated salt solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by rotoevaporation

Sources & evidence

ORD record
ord-9865a37380e546368ba5708807aebdf3
Source dataset
uspto-grants-1999_02
Patent number
US05872126

Reaction notes

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