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palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; for 16h;Heating / reflux; |
A mixture of commercially available 1-boc piperazine (500.1 mg, 2.685 mmol) and commercially available <strong>[262587-05-3]3-difluoromethoxybromobenzene</strong> (598.8 mg, 2.685 mmol) in toluene (20 ml) is placed in a 50 ml three-necked round-bottomed flask made inert with argon, and then the ligand (R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (56.850 mg, 91.2 mumol) and palladium(II)acetate (20.4 mg, 91.2 mumol) are added. The reaction mixture is stirred and brought to reflux for 16 hours. After returning to 20 C., the reaction mixture is diluted with water (20 ml) and then extracted with ethyl acetate (2*30 ml). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The compound obtained is purified by chromatography on silica gel (AIT cartridge, Ref. FC-25 Si-BP-SUP, 20-40 mum, eluent dichloromethane, flow rate 20 ml/min). The fractions containing the expected compound are combined and then evaporated under reduced pressure. The expected tert-butyl 4-(3-difluoromethoxyphenyl)piperazin-1-ylcarboxylate is isolated (253 mg), the characteristics of which are as follows: LC/MS analysis: tr=4.18 min, M+H+ 329.31 |
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palladium diacetate; (R)-2,2'-bis(diphenylphosphanyl)-1,1'-binaphthyl; In toluene; for 16h;Heating / reflux; |
Step1: A mixture of 500.1 mg of 1-boc piperazine and 598.8 mg of commercial <strong>[262587-05-3]3-difluoromethoxybromobenzene</strong> is placed in 20 ml of toluene in a 50 ml three-necked flask under an inert atmosphere of argon, followed by addition of 56.85 mg of (R)(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and 20.4 mg of palladium(II) acetate. The reaction mixture is stirred at reflux for 16 hours. After cooling to 20 C., the reaction mixture is diluted with water (20 ml) and then extracted with ethyl acetate (2×30 ml). The organic extracts are combined, dried over magnesium sulfate, filtered and evaporated under reduced pressure. The compound obtained is purified by chromatography on silica gel (AIT cartridge, ref. FC-25 Si-BP-SUP, 20-40 mum, dichloromethane eluent, flow rate of 20 ml/min). The fractions containing the expected compound are combined and then evaporated under reduced pressure. 253 mg of tert-butyl 4-(3-difluoromethoxyphenyl)piperazine-1-carboxylate are thus isolated, the characteristics of which are as follows: LC/MS: RT=4.18 min, M+H+ 329.31 (Micromass machine, LCT model, connected to an HP 1100 machine, HP G1315A diode array detector (200-600 nm), Sedex 65 light-scattering detector; data analyzed with the Micromass MassLynx software; separation on a Hypersil BDS C18, 3 mum (50×4.6 mm) column, eluting with a linear gradient of from 5% to 90% of acetonitrile containing 0.05% (v/v) of trifluoroacetic acid (TFA) in water containing 0.05% (v/v) TFA, over 3.5 minutes at a flow rate of 1 ml/min). |
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