Methyl iodide → 3alpha-N-methyl-nicotinoyloxy,5alpha-pregnan-20-one iodide

HRID 2253818Notes

Reaction equation

HRID 2253818 reaction equation
[C:1]([O:9][C@@H:10]1[CH2:29][CH2:28][C@@:27]2([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:31])[C@H:16]3[CH2:17][CH2:18][C@@H:19]2[C:20](=[O:22])[CH3:21])[CH2:11]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH3:32][I:33]>CC(C)=O>[I-:33].[CH3:32][N:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:1]([O:9][C@@H:10]2[CH2:29][CH2:28][C@@:27]3([CH3:30])[C@@H:12]([CH2:13][CH2:14][C@@H:15]4[C@@H:26]3[CH2:25][CH2:24][C@@:23]3([CH3:31])[C@H:16]4[CH2:17][CH2:18][C@@H:19]3[C:20](=[O:22])[CH3:21])[CH2:11]2)=[O:8])[CH2:3]1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 544380323alpha-Nicotinoyloxy-5alpha-pregnan-20-one

Product 1

HCID 1317180393alpha-N-methyl-nicotinoyloxy,5alpha-pregnan-20-one iodide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3α-nicotinoyloxy-5α-pregnan-20-one (770 mg, 421 g/m, 1.8 mmol) and methyliodide (3.0 mL, 141 g/m, ~20 mmol) in 30 mL of acetone was refluxed gently for 17 hours. The reaction mixture was concentrated in vacuo to give the crude product.

Workup

  1. temperaturewas refluxed gently for 17 hours
  2. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-634b2869ce3a45c5bcef2c451e0fa89d
Source dataset
uspto-grants-1993_08
Patent number
US05232917

Reaction notes

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