2,4-Dimethoxybenzylamine → HCID 18639903, compound

Participants

Reaction Steps

To a solution of (2S,3S)-2-formyl-3-phenyloxirane (430 mg, 2.90 mmol) in 8.0 mL of dichloromethane under nitrogen was added a solution of 2,4-dimethoxybenzylamine (461 mg, 2.75 mmol) in 1.0 mL of dichloromethane via cannula. Residual amine was washed into the reaction flask with 1.0 mL of dichloromethane. Molecular sieves (2.3 g of pellets, 4 Å, activated) were added and the mixture was allowed to stand for 12 hours. This solution was used directly in the cycloaddition after removing and concentrating a small aliquot for spectral analysis: IR (CHCl3) 3016, 1615, 1510 cm-1 ; 1H NMR (CDCl3, 250 MHz) δ 7.40-7.24 (6H, N=CH, ArH), 7.14 (d, 1H, J=8.8 Hz, ArH), 6.52-6.43 (2H, ArH), 4.62 (s, 2H, NCH2Ar), 3.69 (d, 1H, J=1.9 Hz, oxirane CHCHPh), 3.82 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 3.62 (dd, 1H, J=1.9, 7.0 Hz, oxirane CHCHPh).

Provenance & Evidence