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

HRID 1862715Notes

Reaction equation

[CH2:1]=[C:2]1[CH2:6][C@@H:5]([C:7](OC)=[O:8])[C@H:4]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[OH:8][CH2:7][C@@H:5]1[CH2:6][C:2](=[CH2:1])[CH2:3][C@H:4]1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -10 °C

Procedure

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).

Workup

customthe bath was removed
temperatureThe reaction was cooled in an ice/methanol bath
customthe excess LAH was quenched by dropwise addition of acetone
additionThe reaction was then poured into dilute aq. HCl
extractionThe mixture was extracted twice with ether
washthe organic layers were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated
customThe residue was purified by FC (20-30% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-8c43417f703d4a239c588f92e08394ed
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06538002B1

Reaction notes

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