Methyl iodide → HCID 22875671, compound

HRID 2258017Notes

Reaction equation

HRID 2258017 reaction equation
[CH3:1][N:2]1[C:22](=[O:23])[CH2:21][CH2:20][C@@:19]2([CH3:24])[C@H:3]1[CH2:4][C@H:5]([CH3:26])[C@@H:6]1[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:25])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[C:11]([CH3:14])([OH:13])[CH3:12].[CH3:27]I.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[CH3:27][O:13][C:11]([CH3:14])([C@@H:10]1[C@:15]2([CH3:25])[C@H:7]([C@H:6]3[C@H:18]([CH2:17][CH2:16]2)[C@:19]2([CH3:24])[C@H:3]([N:2]([CH3:1])[C:22](=[O:23])[CH2:21][CH2:20]2)[CH2:4][C@@H:5]3[CH3:26])[CH2:8][CH2:9]1)[CH3:12]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22875673HCID 22875673, compound

Product 1

HCID 22875671HCID 22875671, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 20 mg (0.06 mmol) 20-hydroxy-4,7β,20-trimethyl-5α-4-azapregnan-3-one (from Example 2) in 4 ml dry dimethylformamide at 0° C. was added methyl iodide (10 eq, 0.6 mmol) and sodium hydride (5 eq, 0.3 mmol) were added and the reaction was stirred at RT for 48 hours. Aqueous ammonium chloride was added and the reaction mixture was poured onto 100 ml water and extracted with three 25 ml portions of ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, and evaporated. The product was purified via HPLC on a 19×300 mm 8 micron silica column using 5% isopropanol/hexane eluent at 20 ml/min to yield 15 mg (0.04 mmol, 67% yield) of the title compound.

Workup

  1. additionwere added
  2. extractionextracted with three 25 ml portions of ethyl acetate
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe product was purified via HPLC on a 19×300 mm 8 micron silica column

Sources & evidence

ORD record
ord-f1c69bf40b7541b695238dc18b6ac22f
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

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