Diisopropylamine → HCID 19001401, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of diisopropylamine (0.42 mL, 3.0 mmoles) in 10 mL of THF was added, n-butyllithium (1.9 mL of 1.6M, 3.0 mmole) at -78° C. under N2. After 15 min, a solution of the product of Step D (0.5 g, 1.3 mmole) in 3 mL of THF was added dropwise and the dark red solution that formed was stirred at -78° C. for an additional 15 min. Then, p-toluene-sulfonyl cyanide (0.31 g, 1.7 mmole) in 2 mL of THF was added dropwise to the reaction mixture which decolorized near the end of the addition. Saturated aqueous NH4Cl was added and the reaction was allowed to warm to room temperature. The aqueous phase was extracted with ethyl acetate and the combined organic phases were dried (MgSO4) and concentrated (vacuum). The resulting solid was triturated with ether to afford the title compound (0.36 g, 66% yield) as a white solid, mp 227°- 229° C. 1H NMR (CDCl3): δ8.10 (s, 1H), 7.91 (d, 1H), 7.62 (ABq, 4H), 7.30 (m, 2H), 4.79 (d, 1H), 3.81 (d, 1H), 3.41 (m, 1H), 3.04 (m, 1H), 2.68 (m, 1H), 2.15 (td, 1H).

Provenance & Evidence