Compound for use in the treatment of neurogenic orthostatic hypotension
A compound, a riser technology, applied in the field of the treatment of neurogenic orthostatic hypotension
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example 1
[0166] Preparation of tert-butyl 4-(2-hydroxymethylphenyl)piperidine-1-carboxylate
[0167] tert-butyl 4-(2-carboxyphenyl)piperidine-1-carboxylate (5.0 g, 16 mmol, 1.0 equiv) and THF (130 mL, 1.7 mol) were combined under nitrogen at room temperature. Borane dimethyl sulfoxide complex (2.9 mL, 33 mmol, 2.0 equiv) was added dropwise and the mixture was stirred for 5 minutes, then heated at reflux for 1 hour. The mixture was cooled to room temperature and the reaction was quenched by dropwise addition of MeOH (40 mL). The mixture was then concentrated by rotary evaporation and the resulting material was azeotroped with MeOH (2 x 40 mL). The mixture was then diluted with EtOAc (100 mL) and washed with aqueous hydrochloric acid (1M; 2 x 50 mL) followed by saturated aqueous sodium bicarbonate (2 x 50 mL) followed by saturated aqueous sodium chloride (1 x 50 mL) . The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to give 4-(2-hydroxymet...
example 2
[0170] Preparation of tert-butyl 4-[2-(toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylate
[0171] tert-butyl 4-(2-hydroxymethylphenyl)piperidine-1-carboxylate (0.4 g, 1.0 mmol, 1.0 eq) and triethylenediamine (220 mg, 2.0 mmol, 1.4 eq) were dissolved in DCM ( 11 mL, 170 mmol). The mixture was cooled at 0 °C under nitrogen, and p-toluenesulfonyl chloride (290 mg, 1.5 mmol, 1.1 equiv) was added. The resulting mixture was stirred at 0°C for 60 minutes. The mixture was diluted with EtOAc (50 mL) and washed with water (2 x 25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation to give the title compound (500 mg) which was used without further purification.
[0172] 1 H NMR (CDCl 3 )δ (ppm) 7.81 (t, J = 2.0Hz, 1H); 7.79 (t, J = 2.0Hz, 1H); 7.37-7.32 (m, 4H); 7.25-7.21 (m, 1H); 7.21-7.13 (m,1H),5.12(s,2H);4.34-4.12(m,2H);2.81-2.61(m,3H);2.45(s,3H);1.70-1.52(m,4H);1.48(s ,9H).
example 3
[0174] Preparation of 4-[2-(2,4,6-trifluorophenoxymethyl)phenyl]piperidine trifluoroacetate
[0175] tert-butyl 4-[2-(toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylate (2.1 g, 4.7 mmol, 1.0 equiv) was dissolved in MeCN (46 mL, 890 mmol) , and added to potassium carbonate (1.9 g, 14 mmol, 3.0 equiv) and 2,4,6-trifluorophenol (1.0 g, 7.0 mmol, 1.5 equiv). The mixture was shaken overnight at 50°C, then cooled to room temperature. The supernatant was separated from potassium carbonate and other solids. TFA (7 mL, 90 mmol, 20.0 equiv) was added to the supernatant and the mixture was shaken at room temperature overnight. Then, the solution was concentrated and the residue was dissolved in 1:1 acetic acid / water (5.0 mL). Another portion of acetic acid (2.0 mL) was added and the mixture was filtered and purified by preparative HPLC to give the title compound (1.3 g, 97.5% purity). MS m / z:C 18 h 18 f 3 [M+H] of NO + Calculated, 322.13; found, 322.2.
[0176] 1 H NMR...
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