Borane → HCID 178419238, compound

Participants

Reaction Conditions

Reaction Steps

A 250 mL three necked flask fitted with a mechanical stirrer, nitrogen inlet tube, and teflon coated thermocouple probe, was charged with a solution of the free base product of Example 1 Step B (20.7 g, 81.7 mmol) in dry toluene (100 mL). To the stirred solution at 20° C. was added borane-methyl sulfide (10M, 10.0 mL, 100 mmol) over 5 minutes via syringe. The borane reacted immediately in an exothermic reaction (raising the internal temperature from 20° C. to 32° C.) forming a thick white precipitate. With continued stirring, the mixture was allowed to cool to room temperature (20° C.) over a 1 hour period. The mixture was filtered, and the product cake washed with dry toluene (25 mL). The product was dried in vacuo (20° C., 0.01 mBar) to constant weight. Yield 15.7 g (72%) of a white crystal line solid. m.p. 130°-132° C. (dec). 1H NMR (CDCl3) δ7.7-7.1 (m, 10H, Ar--H), 5.15 (s, 1H, --OH), 4.5 (br, 1H, --NH), 4.2 (m, 1H, C2--H), 3.25 (m, 2H, C5--H2), 2.6 (m, 1H, C4--H), 2.3 (m, 1H, C4--H), 1.85 (m, 1 H, C3--H), 1.6 (m, 1H, C3--H), 2.1-0.7 (br, 3H, BH3). 13C NMR (CDCl3) δ145.8, 144.5 (C1', C1"), 129.1, 128.2 (C3', C5', C3", C5"), 127.4, 127.0 (C4', C4"), 125.2, 125.1 (C2', C6', C2", C6"), 76.5 (Cα), 69.6 (C2), 55.6 (C5), 20.6 (C4), 19.9 (C3).

Provenance & Evidence