Methyl iodide → HCID 14307920, compound

HRID 1109921Notes

Reaction equation

HRID 1109921 reaction equation
CI.[CH3:3][C@@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C:20](=[CH:21][CH2:22][C@:6]2([CH3:7])[C@H:5]1[C:24]([O-:26])=[O:25])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3.[CH:27](N(C(C)C)CC)(C)C.[I-]>C(#N)C>[CH3:27][O:25][C:24]([C@H:5]1[C@H:4]([CH3:3])[CH2:9][C@H:8]2[C@H:10]3[C:20](=[CH:21][CH2:22][C@:6]12[CH3:7])[C@:18]1([CH3:19])[C:13](=[CH:14][C:15](=[O:23])[CH2:16][CH2:17]1)[CH2:12][CH2:11]3)=[O:26]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 30165Iodide IonHCID 81531DiisopropylethylamineHCID 22842949HCID 22842949, compound

Product 1

HCID 14307920HCID 14307920, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl iodide (7.9 ml) is added to a solution of 16α-methylandrosta-4,9(11)-dien-3-one 17β-carboxylate (7.9 g) and diisopropylethylamine (17.5 ml) in acetonitrile (175 ml). The mixture is allowed to stand at 20°-25° for 2 hr and then a second addition of amine (9 ml) and iodide (4 ml) is made. The mixture is allowed to stand overnight at 20°-25° and then concentrated under reduced pressure. The residue is partitioned (water and methylene chloride) and the extract is concentrated and chromatographed on silica gel (750 g) . Elution is performed with acetone/methylene chloride (2-5%/98-95%). The appropriate fractions are pooled and concentrated to give the title compound, m.p. 127.5° (acetone-hexane)

Workup

  1. waitto stand overnight at 20°-25°
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is partitioned (water and methylene chloride)
  4. concentrationthe extract is concentrated
  5. customchromatographed on silica gel (750 g)
  6. washElution
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0a54d54a695d4711b7882f550a0c3183
Source dataset
uspto-grants-1994_06
Patent number
US05322943

Reaction notes

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