Reaktion #1867520

Reaktionsgleichung

5-bromo-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

TFA

→

title compound

5-Bromo-6-chloro-3-(2-(S)-azetidinylmethoxy)pyridine hydrochloride

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatiles were then removed under vacuum
2. 2
   Extraktionextracted with methylene chloride, which
3. 3
   Trocknenwas dried over MgSO4
4. 4
   Einengenconcentrated
5. 5
   SonstigeThe residue was chromatographed on a silica gel column
6. 6
   Wascheneluting with methylene chloride:methanol:NH4OH 10:1:0.1
7. 7
   Sonstigeto afford

Vorschrift

To 5-bromo-6-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 66a (360 mg, 0.95 mmol) was added TFA in methylene chloride at 0° C., and the mixture was stirred for 30 minutes. The volatiles were then removed under vacuum. The residue was neutralized with NaHCO3 to pH 8, then extracted with methylene chloride, which was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with methylene chloride:methanol:NH4OH 10:1:0.1 to afford to give the free base of the title compound. The base was converted to the salt by treatment with hydrogen chloride saturated ethanol to give the title compound (224 mg). mp 168°-169° C. MS (DCI/NH3) m/z 277, 279 (M+H)+. 1H NMR (D2O, 300 MHz) δ: 2.69 (dd, J=7.0, 8.5, 2H), 4.06-4.20 (m, 3H), 4.43 (d, J=4.5, 2H), 4.91-4.99 (m, 1H), 7.94 (d, J=3.0, 1H), 8.17 (d, J=3.0, 1H). Anal. Calcd for C9H10N2OBrCl·0.9 HCl: C, 34.83; H, 3.54; N, 9.03. Found: C, 34.85; H, 3.56; N, 8.82. [α]25D =-4.81° (c 0.13, MeOH).

Quelle