Diisopropylamine → HCID 86759643, compound

Participants

Reaction Conditions

Reaction Steps

Step 31a) To a solution of N,N-diisopropylamine (1.1 ml, 9.54 mmol) dissolved in THF (10 mL) cooled to −78° C., was added n-BuLi (1.6 M in hexane, 5.9 mL, 9.54 mmol). The mixture was stirred for 1 h, and a THF (10 mL) solution of cyclopropylsulfonylamine tert-butyl carbamate (1.0 g, 4.52 mmol) was added dropwise, the generated solution was stirred for 1 h. To this solution was added neat iso-butyl iodide (0.57 mL, 5.0 mmol). The reaction mixture was allowed slowly to warm up overnite. The reaction mixture was poured into cold pH 4.0 buffer and the pH was adjusted to <4 and extracted with EtOAc (3×). The combined extracts were dried (MgSO4), concentrated. The residue was chromatographed over SiO2 eluting with EtOAC/Hexanes (0% to 50%) to afford the product in 69% yield (0.87 g) as a white solid: 1H NMR (CDCl3) □ ppm 0.92 (m, 2H), 0.95 (d, J=6.71 Hz, 6H), 1.49 (s, 9H), 1.69 (m, 2H), 1.71 (s, 2H), 1.95 (m, 1H), 6.80 (s, 1H).

Provenance & Evidence