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

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (+−)-trans-4-methylene-2-phenylcyclopentanoate (26.0 g, 128 mmol) prepared as in Step A in THF (600 mL) under nitrogen and cooled to −10° C. was added dropwise over 15 min 1M lithium aluminum hydride (LAH) in THF (193 mL). After 1 h, the bath was removed and the reaction was stirred at RT for 16 h. The reaction was cooled in an ice/methanol bath and the excess LAH was quenched by dropwise addition of acetone. 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 (23.8 g).

Provenance & Evidence