Lithium borohydride → HCID 86679664, compound

Participants

Reaction Steps

A mixture of 1-tert-butyl 3-ethyl(trans)-4-cyclopropylpyrrolidine-1,3-dicarboxylate (9.2 g, 13 mmol) and LiBH4 (1.37 g, 65 mmol) in dry THF (75 mL) was refluxed overnight. TLC (petroleum ether:EtOAc 5:1) indicated the reaction was complete. The reaction mixture was quenched by addition of water (75 mL) and extracted with EtOAc (75 mL). The organic layer was washed with brine (75 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography (silica gel, petroleum ether:EtOAc=20:1 to 3:1) to give the title compound (2.4 g, 76%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ ppm 3.80-3.78 (d, 1H), 3.64-3.49 (m, 3H), 3.19-3.07 (m, 2H), 2.21 (s, 1H), 1.94-1.81 (d, 1H), 1.44-1.42 (d, 9H), 1.14-1.23 (m, 1H), 0.67-0.62 (m, 1H), 0.50-0.48 (d, 2H), 0.14-0.08 (m, 2H). m/z (APCI+) for C13H23NO3 186.0 (M−tBu+H)+.

Provenance & Evidence