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

HRID 232805Notes

Reaction equation

HRID 232805 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-fd3cc8786af443e4bf1b3720d652f9e3
Source dataset
uspto-grants-1997_01
Patent number
US05591733

Reaction notes

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