Diisopropylamine → HCID 59513421, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of hydantoin 2 (830 mg, 2 mmol), N-Cbz-propargylamine (460 mg, 2.43 mmol; prepared according to the literature by Yasuda et al., patent application 2003, US 2003/0004353), CuI (20 mg, 0.1 mmol), PdCl2(PPh3)2 (70 mg, 0.1 mmol) and iPr2NH (850 μL, 6 mmol) in DMF (5 mL) was heated for 15 min at 100° C. (Smith Microwave Synthesizer). The reaction mixture was diluted with EtOAc, washed with 1 M HCl (2×), NaHCO3 (1×), water (3×) and brine (1×), then dried over MgSO4, filtered and concentrated under vacuum. The crude material was subjected to silica gel chromatography (30→50% EtOAc/hexanes) to yield the desired material as a colorless film (598 mg, 57%). 1H NMR (400 MHz, CDCl3) δ 7.89 (m, 2H), 7.21-7.46 (m, 12H), 6.71 (bs, 1H), 4.62 (s, 2H), 4.12 (m, 2H), 3.81 (s, 3H), 1.72 (s, 3H). MS (ES+): 526 (M+H).

Provenance & Evidence