Ammonium Hydroxide → 2-(tetrahydro-2H-pyran-4-yl)acetamide

A 0° C. solution of tetrahydropyran-4-ylacetyl chloride (0.500 g, 3.07 mmol) in THF (25 mL) was treated drop-wise with NH4OH (˜15M, 2.05 mL, ˜30.7 mmol), allowed to warm to RT and stirred overnight. The mixture was concentrated to dryness, co-evaporated with IPA (2×), then suspended in IPA and the solids removed via filtration. The filtrate was concentrated to dryness to afford 2-(tetrahydro-2H-pyran-4-yl)acetamide (510 mg, 116%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.25 (s, 1H), 6.73 (s, 1H), 3.78 (dd, J=11.4, 4.1 Hz, 2H), 3.29-3.19 (m, 2H), 2.15-1.92 (m, 2H), 1.91-1.78 (m, 1H), 1.58-1.48 (m, 2H), 1.23-1.06 (m, 2H); MS (ESI) m/z: 144.1 (M+H+).

1. concentrationThe mixture was concentrated to dryness, co-evaporated with IPA (2×)
2. customthe solids removed via filtration
3. concentrationThe filtrate was concentrated to dryness

ORD record

ord-92a7d9bbd11c4c219b20da95acfa7f94

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2