Phenethylamine → HCID 14444045, compound

Participants

Reaction Conditions

Reaction Steps

Ozone gas was bubbled through a solution of 5 (606 mg, 1 mmol) in CH2Cl2 (20 mL) cooled to −78° C. until its blue color persists within the solution. The excess ozone was purged using argon and phenethylamine (181 mg, 189 μL, 1.5 mmol) was added. The resulting solution was stirred at −78° C. for 1 h and then allowed to warm to r.t. The solvent was removed under reduced pressure and the residue chromatographed on silica gel (0-30% ethyl acetate in hexane) to yield the product as a clear oil which was then recrystallized from ether/hexane (145 mg, 32%): mp 132-134° C.; 1H NMR (CDCl3) δ1.43 (s, 9H, Boc CH3's), 2.81 (t, 2H, NHCH2—CH2—Ph), 3.12 (dd, 1H, 1 of CH2—CO2Bzl), 3.44 (dd, 1H, 1 of CH2—CO2Bzl), 3.55 (t, 2H, NH—CH2—CH2Ph), 5.10 (s, 2H, benzyl CH2), 5.13 (m, 1H, α-CH), 5.51 (d, 1H, urethane NH), 6.92 (br, 1H, amide NH), 7.20 (m, 5H, phenethyl aromatic CH's), 7.30 (m, 5H, benzyl aromatic CH's); FABMS (calculated for C25H31N2O6, 455.2182) m/e 455.2146 (M++1).

Provenance & Evidence