Methyl 4-methylene-2-phenylcyclopentanecarboxylate, trans- → (+-)-trans-1-Hydroxymethyl-4-methylene-2-phenylcyclopentane

Participants

Reaction Steps

To a solution of methyl (+−)-trans-4-methylene-2-phenylcyclopentanoate (5.0 g, 23 mmol) from Step A in THF (30 mL) under nitrogen was added dropwise over 10 min 1M lithium aluminum hydride (LAH) in THF (23 mL). After 2 h at rt, the excess LAH was quenched by dropwise addition of ethyl acetate and the reaction was then poured into dilute aq. HCl. The mixture was extracted twice with ether and the organic layers were washed with brine, dried over sodium sulfate, combined and concentrated. The residue was purified by FC (20-30% ethyl acetate in hexanes) to afford the title product (4.5 g) as a white solid.

Provenance & Evidence