Dichloromethane → HCID 53466556, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of Boc-D-prolinal (0.5 g, 2.5 mmol) in tetrahydrofuran (10 mL) was added ethyltriphenylphosphonium bromide (3.7 g, 10.0 mmol) and cooled to −78° C. Then added dropwise lithium hexamethyldisilazide 1.0 M in THF (12 mL) and continued stirring from −78° C. to rt overnight. Upon completion as determined by TLC (99:1 methylene chloride to methanol with ninhydrin) the mixture was quenched with 20% ammonium chloride solution and extracted with ethyl acetate. The organic washed with brine, dried over sodium sulfate anhydrous and concentrated in vacuo very carefully as the product is volatile. Crude product was purified on silica gel using a 99:1 mixture of methylene chloride to methanol as mobile phase with ninhydrin to develop. Pure fractions were combined and dried to yield tert-butyl-(2R)-2-[(1Z)-prop-1-enyl]pyrrolidine-1-carboxylate. LC-MS m/z (minus t-butyl+1)=156. 1H NMR (CD3OD, 400 Mhz) 5.47-5.41 ppm (m, 1H), 5.34-5.28 (m, 1H), 4.58-4.53 (m, 1H), 3.42-3.34 (m, 3H), 2.14-2.06 (m, 1H), 1.96-1.77 (m, 2H), 1.70-1.58 (m, 3H), 1.42 (s, 9H).

Provenance & Evidence