1-(Diphenylmethyl)azetidine-3-carbonitrile → HCID 58079830, compound

Participants

Reaction Steps

2-bromo-4-(diethoxymethyl)-1-fluorobenzene (Preparation 31, 1 g) and 1-benzhydrylazetidine-3-carbonitrile (2.7 g) were dissolved in anhydrous THF (4 mL). KHMDS (2.2 g) was then added all at once. The solution became dark brown instantaneously. The reaction was stirred at room temperature overnight. An LC-Ms confirms complete conversion into the desired product: [433]˜3.31 minutes and [505]˜3.62 min. Both peaks correspond to desired product: one is the aldehyde, and the other is the acetal. The crude reaction mixture was concentrated to an oil, and loaded on a 80 g SiO2 cartridge, then eluted with a gradient 0-100% ethylacetate in heptane. The desired fractions were collected and concentrated in vacuum. The resulting oil was suspended in methanol and sonicated for 30 sec, and the resulting white powder is filtered and used as such in the next step. 55% yield. LC-MS [505].

Provenance & Evidence