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-b4e76b31171948babfdd0bc09ef08736

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309224B2