Hydrochloric Acid → HCID 68681207, compound

Participants

Reaction Steps

A solution of the methyl ester (B1) (1.59 g, 4.66 mmol) in MeOH (20 ml) was heated with 6N NaOH (2 ml) at 65° C. for 2 h. The reaction mixture was cooled with in an ice-bath, its pH was adjusted to ca. 5 with 0.5N HCl, and extracted with dichloromethane three times. The combined extracts were dried with sodium sulfate, filtered and concentrated to give 1′-(tert-butoxycarbonyl)-2H-spiro[naphthalene-1,4′-piperidine]-4-carboxylic acid. LC-MS: m/e=344.0 (M+H), 288.0 (M+H—C(CH3)3), 244.0 (M+H−Boc). Rt=3.29 min. 1H-NMR (500 MHz, DMSO-d6): 8.05 (dd, 1 H), 7.80 (d, 1 H), 7.68 (t, 1 H), 7.46 (t, 1 H), 6.74 (s, 1H), 4.03 (m, 2 H), 3.71 (s, 2H), 3.4 (m, 2H), 2.21 (td, 2H), 1.46 (s, 9H), 1.45 (m, 2H).

Provenance & Evidence