1,2-Dichloroethane → 4-methyltetrahydro-2H-pyran-4-carboxamide

A mixture of 4-methyltetrahydro-2H-pyran-4-carboxylic acid (2.60 g, 18.0 mmol), HOBt (2.76 g, 18.0 mmol) and EDC (4.49 g, 23.4 mmol) in MeCN (75 mL) was stirred at RT for 3 h, treated with NH4OH (˜15M, 7 mL, ˜105 mmol) and stirred at RT overnight. The mixture was concentrated to dryness, and the residue was partitioned between satd. brine (40 mL) and DCM (100 mL). The aqueous was extracted with THF (50 mL) and DCM (5×30 mL). The combined organics were washed with 10% aq K2CO3 (50 mL), dried over Na2SO4 and concentrated in vacuo to afford 4-methyltetrahydro-2H-pyran-4-carboxamide (1.83 g, 70%). 1H NMR (400 MHz, DMSO-d6): δ 7.14 (s, 1H), 6.86 (s, 1H), 3.60 (dt, J=11.7, 4.5 Hz, 2H), 3.36 (m, 2H), 1.91-1.89 (m, 2H), 1.30 (m, 2H), 1.08 (s, 3H).

1. stirringstirred at RT overnight
2. concentrationThe mixture was concentrated to dryness
3. customthe residue was partitioned between satd
4. extractionThe aqueous was extracted with THF (50 mL) and DCM (5×30 mL)
5. washThe combined organics were washed with 10% aq K2CO3 (50 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-5431c6d80b98459a9c8624971abc9d7e

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09382228B2