Diisopropylamine → HCID 86759643, compound

Temperature

-78 °C

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).

1. stirringthe generated solution was stirred for 1 h
2. temperatureto warm up overnite
3. additionThe reaction mixture was poured into cold pH 4.0 buffer
4. extractionextracted with EtOAc (3×)
5. dry with materialThe combined extracts were dried (MgSO4)
6. concentrationconcentrated
7. customThe residue was chromatographed over SiO2 eluting with EtOAC/Hexanes (0% to 50%)
8. customto afford the product in 69% yield (0.87 g) as a white solid

ORD record

ord-d20fb1e27d0e43f3933ae8e2dd110121

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06878722B2