2-(Phenylmethyl)oxirane → (+)-Styrene oxide

Participants

Reaction Conditions

Reaction Steps

To a stirring solution of cis-(−)-8-benzydryl-1,4-diazabicyclo[3.3.1]nonane 5 (0.100 g, 0.341 mmol) in dry ethanol was added 2,3-epoxypropyl benzene (0.068 g, 0.512 mmol). The reaction mixture was stirred overnight at 65° C. (Procedure A). The diastereomers were separated by preparative TLC using acetone/diethyl ether (20:80) as mobile phase to afford 6a and 6b. Upper Fraction gave 6a (0.026 g, 18%). 1H NMR (400 MHz, CDCl3): δ 1.24-1.43 (2H, m, H-7), 1.54-1.66 (1H, m, H-6a), 2.03-2.06 (1H, m, H6eq), 2.28 (1H, t, J=12.4 Hz, NCH2CH), 2.39 (1H, bs, H-5), 2.57-2.87 (6H, m, NCH2CH, NCH2CH2N, Ph-CH2), 2.98-3.01 (1H, m, H-9ax), 3.10 (1H, bd, J=11.8 Hz, NCH2CH2N), 3.22-3.25 (1H, m, H-9eq) 3.77 (1H, dt, J=4.8 Hz, J=11.2 Hz, H-8ax), 3.84-3.91 (2H, m, CH—OH, (Ph)2CH), 7.11-7.15 (2H, m, ArH), 7.19-7.31 (1H, m, ArH), 7.35-7.38 (2H, m, ArH). [α]25D (oxalate salt)=(−) 24.7° (c 0.42, MeOH).

Provenance & Evidence