Sodium hydride → HCID 6932371, compound

Participants

Reaction Steps

Sodium hydride (0.788 g, 19.71 mmol, 60% suspension in mineral oil) was added to a solution of (1R,3S)-dimethyl 1,2,2-trimethylcyclopentane-1,3-dicarboxylate (1.50 g, 6.57 mmol, from Step 1) in tetrahydrofuran (20 mL) at room temperature. The resulting mixture was heated to reflux for 1 h, cooled to room temperature, and carefully quenched with saturated ammonium chloride (10 mL). After dilution with ethyl acetate (100 mL), the mixture was washed with water, brine, dried (MgSO4), filtered and concentrated to give crude product (1.45 g), which was found to be roughly a 1:1 mixture of the desired (1R,3R)-product and the (1R,3S)-starting material based on 1H NMR analysis. The mixture was taken to the next reaction without purification.

Provenance & Evidence