Hydrochloric Acid → HCID 131723473, compound

Participants

Reaction Steps

A mixture of the compound of Example 2 91.9 mmol) and 4 mL of 2N NaOH in 4 mL methanol was stirred for 2 hours at room temperature. The clear reaction mixture was neutralized by adding 1 N HCl to produce 1,4-dihydro-2,6-dimethyl-4-[cis-3-(hydroxycarbonyl)cyclopentyl]-3,5-pyridine dicarboxylic acid, dimethyl ester. This compound was obtained as a pale crystalline solid: mp 177-179° C.; 1H NMR (DMSO-d6) δ 11.87 (br. s, 1 H), 8.81 (s, 1 H), 3.85 (d, 1 H, J=6.38 Hz), 3.59 (s, 6 H), 2.5 (m, 1 H), 2.22(s, 6 H), 1.6 (m, 4 H), 1.4 (m, 1 H), 1.2 (m, 2 H); 13C NMR (DMSO-d6) δ 177.2, 168.0, 146.3, 99.5, 50.5, 48.1, 41.9, 34.9, 32.2, 27.3, 27.0, 18.1. Analysis calculated for C17H23NO6. 0.67 H2O: C, 58.44; H, 7.02; N, 4.01. Found: C, 58.44; H, 7.10; N, 3.90. A minor trans-isomer was detected but was not isolated.

Provenance & Evidence