Hydrochloric Acid → HCID 22857705, compound

Participants

Reaction Steps

A 0.25 g (0.8 mmol) sample of (S)-N-BOC-2-(3,5-difluorophenoxymethyl)pyrrolidine, from Example 7b above, was dissolved in 10 mL of a 2:1 mixture of formic acid:formaldehyde and stirred for 16 hr at reflux. To this solution was added excess 10% HCl, and the mixture was extracted twice with ethyl acetate. The aqueous layer was adjusted to pH 12 with K2CO3 and then extracted with methylene chloride. The solvent was dried over MgSO4 and removed under vacuum to yield the crude product, which was then triturated with ether as ethanolic HCl was added. Repeated drying and washing with ether gave 0.118 g of title product. MS: 228 (M+H)+. NMR (D2O) δ: 2.01-2.24 (m, 2H), 2.34-2.43 (m, 1H), 3.02 (s, 3H), 3.27 (br s, 1H), 3,78 (br s, 1H), 3.92 (br s, 1H), 4.27 (dd, 1H, J=6, 11 Hz), 4.44 (dd, 1H, J=3, 11 Hz), 6.63-6.71 (m, 3H). Anal. Calcd for C12H16ClF2NO.0.8 H2O: C, 51.82; H, 6.38; N, 5.04; Found: C, 51.77; H, 6.06; N, 4.82.

Provenance & Evidence