Triethylamine → Glycine methyl ester N-(butoxycarbonyl)pipecolinamide

Participants

Reaction Steps

1-(tertButoxycarbonyl)-2-piperidinecarboxylic acid (11.46 g, 1.2 eq), glycine methyl ester hydrochloride (9.42 g), 1-(dimethylaminopropyl)-3-(ethyl)carbodiimide hydrochloride (8.00 g, 1.0 eq) and Et3N (16.3 mL) were reacted as described in Example 1 to give 5.6 g of the title compound as a colorless crystalline solid: mp 118.5-119.5° C. (EtOAc/isooctane 1:3); 1H-NMR (CDCl3) σ 6.60 (br s, 1H, CONH), 4.81 (m, 1H), 3.82-4.35 (complex m, 4H), 3.76 (s, 3H, OMe), 2.89 (m, 1H), 2.32 (m, 1H), 1.33-1.72 (complex m, 4H), 1.49 (s, 9H, tBu); Anal (calcd for C14H24N2O5): C 55.99, H 8.05, N 9.33. Found: C 56.00, H 8.09, N 9.36.

Provenance & Evidence