Dimethylformamide → HCID 85966059, compound

Participants

Reaction Conditions

Reaction Steps

The crude mesylate (2.03 g, 10 mM), sodium azide (3.25 g, 50 mM) and DMF were combined and heated at 80° C. for 2 hr, cooled to rt then the mixture was diluted with EA and thoroughly washed with water (3×100 mL) and brine. The organics were dried, filtered and concentrated then passed through a short silica gel column eluted with 30% ethyl acetate/hexanes to yield 3-(2-azido-ethyl) tetrahydro-furan (1.04 g, 75%). A catalytic amount of 10% palladium on carbon was added to a methanolic solution of the azide (1.04 g, 7.5 mM), the reaction flask was then briefly evacuated under house vacuum and H2 was added via a balloon. The reaction was stirred at rt overnight under an atmosphere of H2, filtered through a plug of celite, which was thoroughly rinsed with MeOH. One molar HCl in Et2O (10 mL) was added then the volatiles were removed to give 2-(cyclopentyl)ethylamine as the HCl salt (51% yield). ESI-MS (m/z) 114 [M+H]+.

Provenance & Evidence