Bromomethylcyclopropane → HCID 86737781, compound

Participants

Reaction Steps

A mixture of 18a (5.00 g, 16.6 mmole), NaHCO3 (2.90 g, 34.6 mmole) and cyclopropylmethyl bromide (2.80 g, 20.8 mmole) in DMF (50 ml) was heated at 100° under argon for 2 hours. The mixture was cooled, filtered from insoluble material and the filtrate evaporated in high vacuum. The residue was dissolved in dilute NH4OH and extracted with three portions of toluene. The toluene was evaporated to give 4.89 g (83%) of crystalline 19a-CPM. Two recrystallizations from ethanol gave analytically pure 19a-CPM, mp 176.5°-178°. NMR: δ 6.56, s, 2H (aromatic); 6.17, S, 1H, (hydroxy proton); 4.23, d, 1H, (H-5α, J=12.5 Hz); 3.78 (CH3O--); 1.30, d, (H-5β); 0.87, d, 3H (7α-CH3, J=6.5 Hz),

Provenance & Evidence