Hydrochloric Acid → HCID 86737782, compound

Participants

Reaction Steps

A mixture of 18b (7.20 g, 22.8 mmole), NaHCO3 (3.84 g, 45.7 mmole) and cyclopropylmethyl bromide (3.70 g, 27.4 mmole) in DMF (100 ml) was heated at 100° under argon for 2.5 hours. The mixture was processed as described for 19a-CPM to give 8.31 g (99%) of 19b-CPM as a foam. NMR: δ 6.90 (aromatic); 6.35, broad s, 1H (hydroxyl proton); 4.23 (H-5α); 3.78 (CH3O--); 1.10, unsymmetrical d, (8β-CH3, J=5 Hz); 0.92 symmetrical d, (7α-CH3, J=6 Hz). The foam was converted to the HCl salt by dissolving the free base in ethanol, adding an excess of concentrated HCl followed by evaporation to dryness. The residue was azeotroped with 1:1 ethanol-toluene, then toluene and finally crystallized from acetone to give 8.24 g (90%) of 19b-CPM.HCl, mp 194°-195°. Recrystallization from acetone gave an analytical sample of 19b-CPM.HCl as the hemi-acetone solvate. The presence of acetone was confirmed by the nmr of 19b-CMP.HCl taken in DMSO-d6.

Provenance & Evidence