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

Participants

Reaction Steps

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).

Provenance & Evidence