Allyl bromide → HCID 19753237, compound

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Reaction Steps

A sodium hydride/mineral dispersion (50%, 2.00 g) is carefully added to a solution of N-(carbobenzyloxy)-5-aminoindan (XVIA, EXAMPLE 41, 8.856 g) in freshly distilled tetrahydrofuran (about 350 ml) at 20° under argon. The reaction is mildly exothermic with evolution of hydrogen gas. Allyl bromide (3.4 ml, 4.8 g) is then added over 1 min. The mixture is stirred at 20°-25° for 1 hr forming a solid. The mixture is then heated at reflux for 3.5 hr then stirred at 20°-25° overnight. An aliquot is taken, poured into water and ethyl acetate, and the organic layer evaporated. NMR analysis indicates complete reaction. The mixture is poured into ethyl acetate (300 ml), and washed with water (2×250 ml). The combined aqueous layers are extracted with ethyl acetate (100 ml). The combined organic layers are washed with saline, dried over magnesium sulfate and concetrated under reduced pressure to give an oil. The residue is purified by gravity filtration thru a silica gel column (2.5 cm×10 cm, 60-200μ), eluting with hexane. The appropriate fractions are pooled and concentrated to give the title compound as an oil. An analytical sample is obtained by MPLC using ethyl acetate/hexane (10/90). NMR (CDCl3, 300 MHz) 7.30, 7.16, 7.06, 6.96, 5.91, 5.16, 5.13, 4.24, 2.88 and 2.07 δ; IR (CHCl3) 2944, 1694, 1400 and 1153 cm-1 ; MS (m/e) 307, 263, 248, 172, 144 and 91, exact mass calculated for C20H21NO2 =307.1572, found 307.1565.

Provenance & Evidence