Reaktion #454278

Reaktionsgleichung

2-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine

TFA

→

title compound

Ausbeute 111.2%

2-chloro-3-(2-(S)-azetidinylmethoxy)pyridine hydrochloride

Ausbeute 111.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe volatile components were then removed under vacuum
2. 2
   workup.ADDITIONThe residue was treated with saturated K2CO3 solution
3. 3
   Extraktionextracted with methylene chloride, which
4. 4
   Trocknenwas dried over MgSO4
5. 5
   Einengenconcentrated
6. 6
   SonstigeThe residue was chromatographed on a silica gel column
7. 7
   Wascheneluting with chloroform:methanol:NH4OH (10:1:0-10:1:0.5)

Vorschrift

To 2-chloro-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from step 121a (469 mg, 1.66 mmol) was added TFA (5 mL) in methylene chloride (5 mL) at 0° C., and the mixture was stirred for 30 minutes. The volatile components were then removed under vacuum. The residue was treated with saturated K2CO3 solution, then extracted with methylene chloride, which was dried over MgSO4 and concentrated. The residue was chromatographed on a silica gel column, eluting with chloroform:methanol:NH4OH (10:1:0-10:1:0.5) to afford the free base of the title compound (217 mg). The base (156 mg) was dissolved in methylene chloride (3 mL) and then converted to the salt by treatment with saturated HCl in ether to give the title compound (142 mg). mp 155-156° C. MS (DCI/NH3) m/z 199, 201 (M+H)+, 216 (M+NH4)+. 1H NMR (D2O, 300 MHz) δ 2.7-2.79 (m, 2H), 4.13-4.24 (m, 2H), 4.44-4.58 (m, 2H), 4.98 (m, 1H), 7.45 (dd, J=4.8, 8.1 Hz, 1H), 7.59 (dd, J=1.5, 8.2 Hz, 1H), 8.03 (dd, J=1.4, 4.5 Hz, 1H). Anal. Calcd. for C9H11N2OCl.1.0 HCl: C, 45.98; H, 5.14; N, 11.91. Found: C, 45.76; H, 5.09; N, 11.64.

Quelle