Diisopropylamine → HCID 67407672, compound

Diisopropylamine (605 μL, 4.30 mmol) was dissolved in THF (8 mL) and cooled to −78° C. nBuLi (1.72 mL, 2.5 M in hexanes, 4.30 mmol) was added and the resulting solution was stirred for 10 min, warmed to room temperature for 30 min and re-cooled to −78° C. 3-Fluoro-pyridine (370 μL, 4.30 mmol) was added drop-wise and the reaction mixture was stirred for 2 h. A solution of N-methoxy-N-methyloxolane-3-carboxamide (685 mg, 4.30 mmol) in THF (4.2 mL) was added drop-wise and the reaction mixture was warmed to room temperature and stirred for 15 min. The reaction mixture was quenched with sat aq NH4OAc (5 mL), diluted with EtOAc (50 mL), washed with water (2×25 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by normal phase column chromatography to give the title compound as a yellow gum (61.0 mg, 10%). LCMS (ES+): 196.0 (M+H)+.

1. additionwas added
2. temperaturere-cooled to −78° C
3. stirringthe reaction mixture was stirred for 2 h
4. temperaturethe reaction mixture was warmed to room temperature
5. stirringstirred for 15 min
6. customThe reaction mixture was quenched with sat aq NH4OAc (5 mL)
7. additiondiluted with EtOAc (50 mL)
8. washwashed with water (2×25 mL)
9. dry with materialdried (MgSO4)
10. concentrationconcentrated in vacuo
11. customThe residue was purified by normal phase column chromatography

ORD record

ord-f9ef90aad4c8444488d428b636413557

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09227967B2