Dimethyl Sulfoxide → HCID 22507594, compound

Participants

Reaction Conditions

Reaction Steps

A commercially available 2 M solution of oxalyl chloride in DCM solution (13.8 mL of 27.6 mmol), obtained from Aldrich Chemical Co., was diluted with anhydrous dichloromethane (50 mL). The solution was cooled to −78° C., and a solution of dimethyl sulfoxide “DMSO” (4.45 ml 62 mmol) in DCM (10 ml) was added over a 45 min period. After the addition was completed a solution of benzyl-(4-hydroxy-butyl)-carbamic acid tert butyl ester (6.9 g, 25 mmol) in DCM (20 mL) was added was added over a 30 min period resulting in a thick white suspension. The reaction mixture was stirred for an additional 15 min followed by the addition of triethylamine TEA (24 mL) over a 30 min period. The cooling bath was removed and stirring was continued for 1 h. The reaction mixture was quenched with water (200 mL) and the layers were separated. The aqueous layer was extracted with ethyl acetate (3×100 mL). The organic layer was washed with water, brine, and dried over Na2SO4. The crude yellow oil was purified by chromatography using a 8:2 ethyl acetate-hexane mixture as eluent to afford N-benzyl-N-(t-butoxycarbonyl)-4-amino-1-butanal (4.41 g, 63%) as a colorless, viscous oil. 1H NMR δ 9.74 (s, 1H); 7.24-7.36 (m, 5H); 4.41 (bs, 2H); 3.18 (bs, 2H); 2.42 (bs, 2H); 1.66 (bs, 2H); 1.50 (bs, 9H). ELSD/MS: m/z 278 [M+H]+.

Provenance & Evidence