تفاعل #73836

معادلة التفاعل

4-chloro-3-fluorophenylmagnesium bromide

4-oxo-piperidine-1-carboxylic acid tert-butyl ester

ammonium chloride

→

title compound

المردود 30.4%

4-(4-Chloro-3-fluoro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

المردود 30.4%

ظروف التفاعل

المعالجة

1. 1
   أخرىthe organic solvent was removed in vacuo
2. 2
   استخلاصThe mixture was extracted with ethyl acetate
3. 3
   غسيلthis extract was washed with brine
4. 4
   تجفيفdried (MgSO4)
5. 5
   ترشيحfiltered
6. 6
   تركيزconcentrated
7. 7
   أخرىto afford a residue which
8. 8
   أخرىwas purified by column chromatography (SiO2)
9. 9
   غسيلeluting with gradient of ethyl acetate/petrol (0% to 20%)

الإجراء التجريبي

A solution of 4-chloro-3-fluorophenylmagnesium bromide (15 ml, 7.5 mmol, 0.5M in THF) was added, under nitrogen, to 4-oxo-piperidine-1-carboxylic acid tert-butyl ester (1.02 g, 5.1 mmol). After 24 hours, saturated ammonium chloride solution was added then the organic solvent was removed in vacuo. The mixture was extracted with ethyl acetate, then this extract was washed with brine, dried (MgSO4), filtered and concentrated to afford a residue which was purified by column chromatography (SiO2), eluting with gradient of ethyl acetate/petrol (0% to 20%) to afford the title compound (511 mg, 30%). 1H NMR (Me-d3-OD) δ 1.48 (9H, s), 1.67 (2H, br.d), 1.92 (2H, td), 3.16-3.29 (2H, m), 3.99 (2H, br.d), 7.27 (1H, dd), 7.38 (1H, dd), 7.42 (1H, t).

المصدر