TERT-BUTYL 3-HYDROXY-4-PHENYLPIPERIDINE-1-CARBOXYLATE synthesis
- Product Name:TERT-BUTYL 3-HYDROXY-4-PHENYLPIPERIDINE-1-CARBOXYLATE
- CAS Number:1000931-04-3
- Molecular formula:C16H23NO3
- Molecular Weight:277.36
100-59-4
![7-Oxa-3-azabicyclo[4.1.0]heptane-3-carboxylic acid, 1,1-dimethylethyl ester](/CAS/GIF/161157-50-2.gif)
161157-50-2
1000931-04-3
The general procedure for the synthesis of N-BOC-3-hydroxy-4-phenylpiperidine from phenylmagnesium chloride and tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate was as follows: referring to the method of Tetrahedron Lett., 1979, 17, 1503, to a stirred tetrahydrofuran (THF, 3 mL) solution of phenylmagnesium chloride (0.753 mL, 1.51 mmol) and copper(I) iodide (0.0191 g, 0.100 mmol) solution of tetrahydrofuran (THF, 3 mL), a THF (1 mL) solution of tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate (0.200 g, 1.00 mmol) was slowly added. The reaction mixture was gradually warmed to room temperature and stirred continuously for 16 hours. Upon completion of the reaction, the reaction was quenched with saturated aqueous ammonium chloride solution, followed by extraction of the mixture with ethyl acetate (AcOEt). The organic layers were combined, dried with anhydrous sodium sulfate, filtered and concentrated in vacuum to afford tert-butyl 3-hydroxy-4-phenylpiperidine-1-carboxylate (0.261 g, 94% yield) as an oil. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 1.49 (s, 9H), 1.76 (m, 3H), 2.50-2.78 (m, 3H), 3.70 (m, 1H), 4.30 (bd, 1H), 7.30 (m, 5H).
100-59-4
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161157-50-2
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1000931-04-3
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$45.00/10mg
Yield:1000931-04-3 94%
Reaction Conditions:
Stage #1: phenylmagnesium chloride;tert-butyl 7-oxa-3-azabicyclo[4.1.0]heptane-3-carboxylate;copper(l) iodide in tetrahydrofuran at -30 - 25; for 16 h;
Stage #2: with water;ammonium chloride in tetrahydrofuran;
Steps:
4
According to Tetrahedron Lett., 1979, 17, 1503, to a stirred solution of phenylmagnesium chloride (0.753 mL, 1.51 mmol) and copper (I) iodide (0.0191 g, 0.100 mmol) in THF (3 mL) at -300C was added tert-butyl 7-oxa-3-aza- bicyclo[4.1.0]heptane-3-carboxylate (0.200 g, 1.00 mmol) in THF (1 mL) . The mixture was allowed to warm to room temperature and was stirred for 16 h. It was then quenched with saturated aqueous ammonium chloride and the mixture was extracted with AcOEt. The combined organic layers were dried (sodium sulfate) , filtered, and concentrated in vacuo to give tert-butyl 3-hydroxy-4-phenylpiperidine-l-carboxylate (0.261 g, 94%) as an oil: 1H NMR (400 MHz, DMSO-d6) δ 1-49 (s, 9H), 1.76 (m, 3H), 2.50-2.78 (m, 3H), 3.70 (m, IH), 4.30 (bd, IH), 7.30 (m, 5H).
References:
WO2008/11130,2008,A2 Location in patent:Page/Page column 136-137
85838-94-4
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1000931-04-3
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$45.00/10mg