CAS No. : | 847728-89-6 | MDL No. : | MFCD11506011 |
Formula : | C13H18BrNO2 | Boiling Point : | No data available |
Linear Structure Formula : | - | InChI Key : | KECPRZHCNCDSET-VIFPVBQESA-N |
M.W : | 300.19 | Pubchem ID : | 56973617 |
Synonyms : |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In dichloromethane; at 20.0℃; | Description 1 : (S)-tert-butyl (1-(4- romophenyl)ethyl)carbamate (D1)A mixture of (S)-(-)-1 -(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd No.B157615), di-tert-butyl dicarbonate (8.72 g, 1 .05 mmol), and triethylamine (16ml, 1 14 mmol) in dichloromethane (120ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200ml) and washed with water (100ml). The organic solution was dried over Na2S04 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid.1 H NMR (400MHz ,CHLOROFORM-d) δ (ppm): 7.47- 7.42 (2H, m), 7.18 (2H, d, J= 8.4 Hz), 5.30 (2H, br s), 1 .41 (12H, br s). | |
12.7 g | With triethylamine; In dichloromethane; at 20.0℃; | A mixture of (S)-(-)-1-(4-Bromophenyl)ethylamine hydrochloride (9 g, 38.0 mmol, available from Bepharm Ltd B157615), di-tert-butyl dicarbonate (8.72 g, 1.05 mmol), and triethylamine (16 ml, 114 mmol) in dichloromethane (120 ml) was stirred at room temperature overnight. The mixture was diluted with dichloromethane (200 ml) and washed with water (100 ml). The organic solution was dried over Na2SO4 and solvents were evaporated in vacuo to afford the title compound (D1) (12.7 g) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium acetate; | Step 1 A flask was charged with tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.4 g, 4.66 mmol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.42 g, 5.60 mmol, 1.2 eq), <strong>[72287-26-4](1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride</strong> (170 mg, 0.23 mmol, 0.05 eq), potassium acetate (915 mg, 9.33 mmol, 2 eq) and dioxane (30 mL). The mixture was purged with nitrogen for 10 min, then heated to 80 C. for 1 h. The reaction mixture was cooled to 20 C. and filtered through a pad of celite. The filtrate was concentrated in vacuum. The crude product was purified by column (petroleum ether:ethyl acetate=10:1). Tert-butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.9 g, crude) was obtained as a colorless oil. | |
With potassium acetate; | Step 3 A flask was charged with tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.4 g, 4.66 mmol, 1 eq), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (1.42 g, 5.60 mmol, 1.2 eq), <strong>[72287-26-4](1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride</strong> (170 mg, 0.23 mmol, 0.05 eq), potassium acetate (915 mg, 9.33 mmol, 2 eq) and dioxane (30 mL). The mixture was purged with nitrogen for 10 minutes, then heated to 80 C. for 1 hour. The reaction mixture was cooled to 20 C. and filtered through a pad of celite. The filtrate was concentrated in vacuum. The crude product was purified by flash chromatography (petroleum ether:ethyl acetate=10:1). Tert-Butyl N-[(1S)-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]ethyl]carbamate (1.9 g, crude) was obtained as a colorless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium carbonate; | Step 2 Into a 250-mL round-bottom flask, was placed tert-butyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate (1.0 g, 3.331 mmol, 1 equiv), <strong>[1047644-76-7]1,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole</strong> (1.48 g, 6.664 mmol, 2.00 equiv), K2CO3 (1.38 g, 9.963 mmol, 2.99 equiv) and Pd(dppf)Cl2 (244.0 mg, 0.333 mmol, 0.10 equiv) in dioxane (16 mL) and H2O (2 mL). The resulting mixture was stirred for 3 hours at 90 C. under nitrogen atmosphere. The mixture was concentrated under reduced pressure. The residue was applied onto a silica gel column eluting with ethyl acetate/petroleum ether (1:1). This resulted in 1.63 g (99%) of benzyl N-[(1S)-1-(4-bromophenyl)ethyl]carbamate as a light yellow solid. |
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