2-(Phenylmethyl)oxirane → HCID 44450675, compound

Participants

Reaction Steps

Compound 3 (0.075 g, 0.281 mmol) was reacted with S-(−)-2,3-epoxypropyl benzene (0.056 g, 0.422 mmol) (Procedure A) and was purified by flash column chromatography over silica gel using diethyl ether/MeOH/Et3N (90:10:0.2) to yield 4d (0.037 g, 33%). 1H NMR (400 MHz, CDCl3): δ 1.23-1.35 (2H, m, H-5), 1.41-1.49 (1H, m, H-4ax), 1.75-1.78 (1H, m, H-4eq), 2.36-2.41 (1H, dd, J=3.2 Hz, J=8.8 Hz, NHCH2), 2.66-2.84 (5H, m, H-2, NHCH2, Ph-CH2), 2.89-2.92 (1H, m, H-3eq), 3.23 (1H, dt, J=2.4 Hz, J=10.0 Hz, H-6ax), 3.75 (1H, d, J=10.0 Hz, (Ph)2CH) 3.78-3.85 (1H, m, and CH—OH), 7.12-7.31 (13H, m, ArH), 7.35-7.36 (2H, m, ArH). Optical rotation, [α]25D=(−) 49.3° (c 0.96, MeOH). Free base was converted into oxalate salt 206-209° C.

Provenance & Evidence