Triphenylphosphine → Methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate

温度

70 °C

To a stirred solution of methyl 2-hydroxypyridine-5-carboxylate (269.8 mg, 1.762 mmol), N-tert-butoxycarbonylprolinol (354.6 mg, 1.762 mmol), and Ph3P (554.6 mg, 2.114 mmol) in THF (10 mL) was slowly added DIAD (0.42 mL, 2.114 mmol) at room temp, and the resulting mixture was stirred for 6 hr at 70° C. The reaction mixture was concentrated and the residue was chromatographed on silica-gel with n-hexane:EtOAc (5:1, v/v) as eluent to give 262.5 mg (44%) methyl 2-[[1-(tert-butoxycarbonyl)-2-pyrrolidinyl]methoxy]pyridine-5-carboxylate as an oil. 1H-NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.85–1.98 (m, 4H), 3.37 (br s, 2H), 3.92 (s, 3H), 4.12–4.33 (br m, 2H),4.4 (br s, 1H),6.75(m, 1H),8.15 (m, 1H), 8.79 (m, 1H); MS (FAB) m/z 337 (M++1).

1. customat room temp
2. concentrationThe reaction mixture was concentrated
3. customthe residue was chromatographed on silica-gel with n-hexane:EtOAc (5:1

ORDレコード

ord-c6f128d5496a46e484b4e24bc3c136e3

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07179819B2