Methyl iodide → HCID 14307920, compound

HRID 1769905Notes

Reaction equation

HRID 1769905 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-34f1167f6c0f45c0951701fcf6307987
Source dataset
uspto-grants-1995_01
Patent number
US05382661

Reaction notes

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