1,2-Dichloroethane → Oxane-4-carboxamide

Temperature

0 °C

A 0° C. solution of tetrahydro-2H-pyran-4-carboxylic acid (0.5 g, 3.84 mmol) in MeCN (15 mL) was treated with EDC (0.884 g, 4.61 mmol) and HOBT (0.706 g, 4.61 mmol) under an argon atmosphere and stirred at 0° C. for 1 h. Ammonium hydroxide (˜15M, 0.512 mL, 7.68 mmol) was added slowly and the mixture was warmed to RT and stirred overnight. The mixture was treated with water, saturated with solid NaCl and the aqueous layer was extracted with THF (2×). The combined organics were washed with brine, dried over Na2SO4 and concentrated to afford tetrahydro-2H-pyran-4-carboxamide (0.23 g, 46%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.20 (s, 1H), 6.73 (s, 1H), 3.82-3.81 (m, 2H), 3.30-3.21 (m, 2H), 2.30-2.27 (m, 1H), 1.60-1.46 (m, 4H).

1. temperaturethe mixture was warmed to RT
2. stirringstirred overnight
3. extractionthe aqueous layer was extracted with THF (2×)
4. washThe combined organics were washed with brine
5. dry with materialdried over Na2SO4
6. concentrationconcentrated

ORD record

ord-26597227013d4270a58f748012e5294f

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2