Phenethyl bromide → HCID 21904372, compound

Participants

Reaction Steps

A solution of 213 (0.302 mmol, 127 mg) in CH3OH (1 mL) at 25° C. was treated with 30% Pd-C (25 mg) and then placed under a hydrogen atmosphere. The reaction mixture stirred for 12 h and then was filtered through a pad of celite. The solvents were removed in vacuo and the resulting oil was then treated with phenethyl bromide (1.5, equiv, 0.453 mmol, 62 μL) and K2CO3 (2.0 equiv, 0.604 mmol, 83 mg) in CH3CN (1.0 mL). The reaction mixture stirred for 12 h at 65° C. The reaction mixture was then purified directly by chromatography (PTLC, SiO2, 20 cm×20 cm, 1 mm, EtOAc-10% CH3OH) which provided 214 (51 mg, 118 mg theoretical, 43%) as colorless oil: Rf 0.45 (SiO2, EtOAc-10% CH3OH); LRMS m/z 390 (M+, C26H34N2O, requires 390).

Provenance & Evidence