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[ CAS No. 849928-30-9 ]

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2D
Chemical Structure| 849928-30-9
Chemical Structure| 849928-30-9
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Product Details of [ 849928-30-9 ]

CAS No. :849928-30-9MDL No. :MFCD04035609
Formula : C16H21NO3 Boiling Point : 400.8°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :275.34Pubchem ID :44558601
Synonyms :

Computed Properties of [ 849928-30-9 ]

TPSA : 46.6 H-Bond Acceptor Count : 3
XLogP3 : 2.1 H-Bond Donor Count : 0
SP3 : 0.50 Rotatable Bond Count : 3

Safety of [ 849928-30-9 ]

Signal Word:WarningClass:N/A
Precautionary Statements:P261-P280-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 849928-30-9 ]

  • Downstream synthetic route of [ 849928-30-9 ]

[ 849928-30-9 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 849928-30-9 ]
  • [ 109-94-4 ]
  • 5-hydroxymethylene-4-oxo-2-phenyl-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride; In methanol; benzene; at 20℃; Synthesis of 5-hydroxymethylene-4-oxo-2-phenyl-piperidine-1-carboxylic acid tert-butyl ester (51). To a suspension of the <strong>[849928-30-9]piperidin-4-one</strong> (50) (442 mg, 1.61 mmol) and 75 mg of NaH (60% suspension in mineral oil, 1.77 mmol) in 10 ml of benzene were added 1.3 ml of ethyl formate and 40 ml of methanol. The mixture was stirred at room temperature overnight. Water (5 ml) was added and the organic layer was separated. NaHSO4 (10% Aq) was added to the aqueous layer to adjust pH to the range of 3-4 and then extracted with EtOAc twice (2 x 10 ml). Combined organic layers were washed with brine (5 ml) once, and dried (MgSO4). After evaporation of solvent, the yellow oil was used for the next reaction without further purification. LCMS 326.1 (M + 23)
  • 3
  • [ 849928-30-9 ]
  • 2-phenylpiperidin-4-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% General ProcedureTo a solution of the 2-substituted N-BOC piperidone in DCM (0.15 M) was added TFA (2 ml per mmol) at O0C. This solution was allowed to stir for 1 h before being poured on to solid potassium carbonate (~25 eq.). This mixture was dissolved in water and extracted with diethyl ether (x 3). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. The crude material was re-dissolved in DCM and cooled to O0C and to this was added triethylamine (3 eq.) followed by acetyl chloride (2 eq.). After stirring for 14 h, the reaction was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate (x 3). The combined organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (eluant; hexane : ethyl acetate) then proceeded to afford the desired product as a pale yellow oil.iV-Acetyl-2-phenyl-4-oxopiperidine-l-carboxylateC13H15NO2, MoI. Wt: 217.26Pale yellow oil, 634 mg, 80% (over 2 steps = 93% per step). EPO <DP n="220"/>1H NMR: (CDCl3, 400 MHz): delta 2.18 (LlH, s, CH3), 2.25 (1.9H5 s, CH3), 2.38 (0.37H5 s, CH)5 2.42 (0.63H5 S5 CH)5 2.47-2.55 (IH5 m5 CH), 2.78-2.93 (IH5 m, CH)5 3.00 (0.63H5 S5 CH)5 3.04 (0.37H5 S5 CH)5 3.26-3.33 (IH5 m5 CH)5 3.84-3.87 (0.63H5 m5 CH)5 4.57-4.60 (0.37H5 m, CH)5 5.37 (0.37H5 S5 CH)5 6.37 (0.63H5 d5 J = 5.6 Hz5 CH)5 7.21-7.39 ppm (5H5 m, 5 x ArH).
  • 4
  • [ 849928-30-9 ]
  • [ 109-94-4 ]
  • C17H21NO4 [ No CAS ]
  • 5
  • [ 849928-30-9 ]
  • [ 1779-49-3 ]
  • [ 1257300-02-9 ]
YieldReaction ConditionsOperation in experiment
96% A suspension of potassium tert-butoxidc (1.25 g, 11.1 mmol) and methyltriphenylphosphonium bromide (3.86 g, 1.1 mmol) in tetrahydrofuran (100 mL) was stirred at 40 0C for 30 minutes. The mixture was then cooled to room temperature and a solution of tert-butyl 4-oxo-2-phenylpiperidine-l-carboxylate (2.35 g, 8.5 mmol) in tetrahydrofuran (30 mL) was added slowly. The reaction mixture was stirred at 40 0C for 24 hours. The mixture was cooled to room temperature and quenched by the addition of water and diluted with ethyl acetate (250 mL), The organic layer was separated then washed with water, 10% aqueous citric acid and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica gel (hexane:ethyl acetate 95:5 to 9:1) provided tert-butyl 4-methylene-2- phenylpiperidine-1-carboxylate (2.24 g, 96%). 1H NMR (400 MHz, CDCl3): 7.31 (m, 4H), 7.21 (m, IH), 5.48 (br d, IH), 4.84 (dd, 2H), 4.07 (br dd, IH), 2.85 (br, t, IH), 2.78 (dtr, IH), 2.64 (dd, IH), 2.28 (dtr, IH), 2.20 (br d, IH), 1.42 (s, 9H). GC/MS (EI) for CnH23NO2: 273 (M+).
96% A suspension of potassium te/t-butoxide (1.25 g, 11.1 mmol) and methyltriphenylphosphonium bromide (3.86 g, 1.1 mmol) in tetrahydrofuran (100 mL) was stirred at 40 0C for 30 minutes. The mixture was then cooled to room temperature and a solution of tert-butyl 4-oxo-2-phenylpiperidine-l-carboxylate (2.35 g, 8.5 mmol) in tetrahydrofuran (30 mL) was added slowly. The reaction mixture was stirred at 40 0C for 24 hours. The mixture was cooled to room temperature and quenched by the addition of water and diluted with ethyl acetate (250 mL), The organic layer was separated then washed with water, 10% aqueous citric acid and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica gel (hexane: ethyl acetate 95:5 to 9:1) provided tert-butyl 4-methylene-2-phenylpiperidine-l-carboxylate (2.24 g, 96%). 1H NMR (400 MHz, CDCl3): 7.31 (m, 4H), 7.21 (m, IH), 5.48 (br d, IH), 4.84 (dd, 2H), 4.07 (br dd, IH), 2.85 (br, t, IH), 2.78 (dtr, IH), 2.64 (dd, IH), 2.28 (dtr, IH), 2.20 (br d, IH), 1.42 (s, 9H). GC/MS (EI) for Ci7H23NO2: 273 (M+).
96% A suspension of potassium tert-butoxide ( 1.25 g, 11.1 mmol) and methyltriphenylphosphonium bromide (3.86 g, 1.1 mmol) in tetrahydrofuran (100 mL) was stirred at 40 C for 30 minutes. The mixture was then cooled to room temperature and a solution of tert-butyl 4-oxo-2-phenylpiperidine-l-carboxylate (2.35 g, 8.5 mmol) in tetrahydrofuran (30 mL) was added slowly. The reaction mixture was stirred at 40 C for 24 hours. The mixture was cooled to room temperature and quenched by the addition of water and diluted with ethyl acetate (250 mL), The organic layer was separated then washed with water, 10% aqueous citric acid and brine, dried over anhydrous sodium sulfate, filtered and concentrated. Column chromatography on silica gel (hexane:ethyl acetate 95:5 to 9:1) provided tert-butyl 4-methylene-2-phenylpiperidine-l-carboxylate (2.24 g, 96%). NMR (400 MHz, CDCI3): 7.31 (m, 4H), 7.21 (m, 1H), 5.48 (br d, 1H), 4.84 (dd, 2H), 4.07 (br dd, 1H), 2.85 (br, t, 1H), 2.78 (dtr, 1H), 2.64 (dd, 1H), 2.28 (dtr, lH), 2.20 (br d, 1H), 1.42 (s, 9H). GC/MS (EI) for C7H23NO2: 273 (M+).
To a solution of methyl triphenylphosphonium bromide (5 g, 14 mmol) in THF (30 mL) at -78C was added n-BuLi (2.5 M, 5.5 mL, 13.75 mmol). The mixture was then stirred at -78 C for 5mm, and then stirred at 0 C for 0.5h. To the mixture at -78 C was then added a solution of (±)- <strong>[849928-30-9]tert-butyl 4-oxo-2-phenylpiperidine-1-carboxylate</strong> (2 g, 7.26 mmol) in THF (10 mL). The mixture was stirred at room temperature for 1 5h, and then stirred at 40 C for 3h. The reaction was quenched with MeOH (10 mL), and then diluted with Et20. The mixture was then filtered through aplug of Celite, which was rinsed with Et20. The filtrate was concentrated. The resulting residue was purified by silica gel flash column chromatography (heptane/EtOAc = 81/1 9) to afford the title compound. MS (ESl+) m/z 274.4 (M+H).

  • 6
  • [ 849928-30-9 ]
  • [ 75-16-1 ]
  • (+/-)-tert-butyl (2R,4R)-4-methyl-2-phenylpiperidin-4-ol-1-carboxylate [ No CAS ]
  • (+/-)-tert-butyl (2R,4S)-4-methyl-2-phenylpiperidin-4-ol-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
35%; 29% Methylmagnesium bromide (3 M solution in ether, 1.2 mL, 3.6 mmol) was added to a solution of tert-butyl 4-oxo-2-phenylpiperidine-l -carboxylate (328 mg, 1.2 mmol), in tetrahydrofuran (20 mL) at 0 0C and the resulting mixture was stirred at this temperature one hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (20 mL) and diluted with ethyl acetate (80 mL). The organic portion was separated, washed with water, then brine solution, dried over sodium sulfate, filtered and concentrated. The residue purified by silica gel chromatography (25% to 70% ethyl acetate in hexane gradient) to give the first elueting isomer assigned as (+/-)-tert-butyl (2i?,45)-4-methyl-2-phenylpiperidin-4-ol-l -carboxylate (100 mg, 29% yield), LC-MS for Ci7H25NO3: 292 (MH+); and the second elueting isomer assigned as (+/-)-tert-butyl (2R,4R)-4- methyl-2-phenylpiperidin-4-ol-l -carboxylate (120 mg, 35% yield), MS (EI) for Ci7H25NO3: 292 (MH+).
35%; 29% Methylmagnesium bromide (3 M solution in ether, 1.2 mL, 3.6 mmol) was added to a solution of teri-butyl 4-oxo-2-phenylpiperidine-l -carboxylate (328 mg, 1.2 mmol), in tetrahydrofuran (20 mL) at 0 C and the resulting mixture was stirred at this temperature one hour. The reaction mixture was then quenched with saturated aqueous ammonium chloride solution (20 mL) and diluted with ethyl acetate (80 mL). The organic portion was separated, washed with water, then brine solution, dried over sodium sulfate, filtered and concentrated. The residue purified by silica gel chromatography (25% to 70% ethyl acetate in hexane gradient) to give the first elueting isomer assigned as (+/-)-tert-butyl (2/?,45)-4-methyl-2-phenylpiperidin-4-ol-l -carboxylate (100 mg, 29% yield), LC-MS for C17H25NO3: 292 (MH*); and the second elueting isomer assigned as (+/-)-tert-butyl (2R,4R)-4- methyl-2-phenylpiperidin-4-ol-l -carboxylate (120 mg, 35% yield), MS (EI) for C17H25NO3: 292 (MIT).
  • 7
  • [ 849928-30-9 ]
  • [ 202289-38-1 ]
  • [ 1257300-29-0 ]
YieldReaction ConditionsOperation in experiment
81% In dichloromethane; at 0 - 20℃; To a solution of tert-butyl 4-oxo-2-phenylpiperidine-l-carboxylate (0.20 g, 0.73 mmol), in dichloromethane (50 mL) at 0 0C was slowly added bis (2-methoxyethyl) aminosulfur trifluoride (0.16 mL, 0.87 mmol) and the reaction mixture was allowed to warm to room temperature. The mixture was stirred for 12 hours, then quenched by the addition of saturated aqueous ammonium chloride and partitioned with ethyl acetate. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. Silica gel chromatography of the residue (hexanes: ethyl acetate 4:1) provided tert-butyl 4,4-difluoro-2-phenylpiperidine-l-carboxylate (0.17 g, 81%). GC-MS (EI) for Ci6H2IF2NO2: 241 (M-tBu+).
  • 8
  • [ 849928-30-9 ]
  • (+/-)-(2R,4S)-4-methyl-2-phenylpiperidin-4-ol trifluoroacetate [ No CAS ]
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