Hydrochloric Acid → HCID 70208604, compound

Participants

Reaction Steps

A solution of 2-(1-BOC-2-(S)-pyrrolidinyl)-7-chlorofuro[3,2-b]pyridine, from step 51a above, in HCO2H (15.0 mL, 88%) and H2CO (15 mL, 37%) was refluxed for one hour. After cooling to room temperature and the solution was acidified to pH=2.0 with 1 N aqueous HCl and washed with Et2O (150 mL). The aqueous layer was basified with 15% NaOH and extracted with CH2Cl2 (4×400 mL). The combined CH2Cl2 extracts were dried (MgSO4) and concentrated. The crude material was chromatographed (silica gel; CH2Cl2 :MeOH, 95:5) to afford the title compound as a light yellow oil (0.036 g, 15%). The amine was dissolved in Et2O and cooled to 0° C. and a saturated solution of HCl in Et2O was added until precipitation ceased. The solvent was removed and the yellow solid was placed under vacuum to afford the title compound: [α]D≤ +26.24 (c 0.05, H2O); 1H NMR (D2O, 300 MHz) δ 2.28-2.42 (m, 2H), 2.50-2.68 (m, 2H), 2.98 (s, 3H), 3.42 (br s, 1H), 3.62 (br s, 1H), 5.00 (m, 1H), 7.38 (s, 1H), 7.59 (d, J=6.0 Hz, 1H), 8.44 (d, J=6.0 Hz, 1H); MS (DCI/NH3) m/z: 237 (M+H)+ ; Anal. Calcd for C12H13N2O.1.2 HCl.0.10H2O.0.20Et2O: C, 51.75; H, 5.56; N, 9.43. Found C, 51.40; H, 5.49; N,9.03.

Provenance & Evidence