반응 #453015

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

triethylamine

1-hexyne

CH2Cl2

→

title compound

수율 56.0%

5-Hexynyl-3-(2-(S)-azetidinylmethoxy)pyridine dihydrochloride

수율 56.0%

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후처리

1. 1
   온도The mixture was refluxed overnight
2. 2
   기타The solvent was removed
3. 3
   기타the residue was chromatographed on a silica gel column
4. 4
   세척eluting with EtOAc:hexane 1:1

실험 절차

To a solution of 5-bromo-3-(1-BOC-2-(S)-azetidinylmethoxy)pyridine from Example 54b (180 mg, 0.48 mmol), bis(triphenylphosphine)palladium(II) chloride (7 mg, 0.05 mmol), copper (I) iodide (2 mg) and triethylamine (1.0 mL) in CH2Cl2 (3 mL) was added 1-hexyne (8.3 mL, 0.72 mmol). The mixture was refluxed overnight and cooled to room temperature. The solvent was removed, and the residue was chromatographed on a silica gel column, eluting with EtOAc:hexane 1:1 to afford the title compound (102 mg, 56% yield). MS (CI/NH3) m/z 379 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ0.96 (t, J=6.6 Hz, 3H), 1.43 (s, 9H), 1.46-1.69 (m, 4H), 2.20-2.40 (m, 2H), 2.44-2.56 (m, 2H), 3.83-3.92 (m, 2H), 4.06-4.15 (m, 1H), 4.26-4.38 (m, 1H), 4.45-4.57 (m, 1H), 7.34 (br s, 1H), 7.51-7.58 (m, 1H).

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