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CAS No. : | 112022-83-0 | MDL No. : | MFCD00078440 |
Formula : | C18H20BNO | Boiling Point : | No data available |
Linear Structure Formula : | NCH2CH2CH2CHC(C6H5)2OBCH3 | InChI Key : | VMKAFJQFKBASMU-QGZVFWFLSA-N |
M.W : | 277.17 | Pubchem ID : | 9838490 |
Synonyms : |
|
Chemical Name : | (R)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P264-P270-P280-P305+P351+P338-P310-P330-P403-P501 | UN#: | |
Hazard Statements: | H302-H319 | 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 |
---|---|---|
A solution of [[(R)-TETRAHYDRO-1-METHYL-3, 3-DIPHENYL-1 H, 3H-PYRROLO] [1, [2-C]] [1,3, 2] - oxazaborole] [(1 M, 424, UL)] in THF (2ml) was added to borane dimethylsulfide complex (2M, 212. 7l) in THF [(15ML)] and stirred at [0C] for 10 min. The reaction mixture was cooled to-10C and treated with a solution of 8-benzyloxy-5-bromoacetylcarbostyril (EP 147719A2) (791mg) in THF [(16MOI)] over 20 min. Further borane dimethylsulfide complex (1. [28MUT)] was added over 4 h at [0C.] The reaction mixture was stirred for a further hour at [0C] prior to quenching with methanol and [1 N HCI] (aq). The reaction mixture was partitioned between water and ethyl acetate. The organic phase was dried and concentrated in vacuo. The residue was triturated with hexane-ethyl acetate to afford the title compound (700mg). Rf (EtOAc) 0.47 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In tetrahydrofuran; hydrogenchloride; ethyl acetate;liquid HCl; | Step 2: (R)-8-(Benzyloxy)-5-(2-bromo-1-hydroxyethyl)quinolin-2(1H)-one 8-(Benzyloxy)-5-(2-bromoacetyl)quinolin-2(1H)-one (26.0 g, 69.9 mmol) and (R)-3,3-diphenyl-1-methyltetrahydro-3H-pyrrolo[1,2-c][1,3,2]oxazaborole (21.3 g, 76.8 mmol) were azeotroped with toluene (*3) then suspended in anhydrous THF (400 mL) under an atmosphere of nitrogen. The suspension was cooled to -20 C. (external temperature) and borane dimethyl sulfide (BH3-Me2S) complex solution (45.4 mL, 90.8 mmol, 2.0 M solution in THF) was added by syringe pump over 3 hours. After complete addition the reaction mixture was stirred for one hour before quenching with methanol (25 mL). The reaction was warmed to RT over 20 minutes. The mixture was concentrated under reduced pressure and the residue was suspended in aqueous hydrochloric acid (500 mL, 1 M solution) and stirred at RT for 18 hours. After this time the solid was collected by filtration and washed with water (3*100 mL). The solid was partially dissolved in ethyl acetate and heated at reflux for 2 hours. The remaining solid was removed by hot filtration and the filtrate was evaporated to afford the title compound. The solid collected from the hot ethyl acetate was again partially dissolved in ethyl acetate and heated at reflux for 2 hours then filtered to give filtrate containing pure product. This process was repeated four more times. The combined solid was recrystallised from ethyl acetate and petroleum ether to afford the title compound (20.0 g, 76%). 1H NMR (400 MHz, DMSO-d6): delta 10.68 (s, 1H); 8.19 (d, J=9.9 Hz, 1H); 7.58 (d, J=7.5 Hz, 2H); 7.41-7.36 (m, 2H); 7.34-7.29 (m, 1H); 7.23-7.19 (m, 2H); 6.57 (d, J=9.8 Hz, 1H); 5.94 (d, J=4.7 Hz, 1H); 5.31 (s, 2H); 5.25-5.19 (m, 1H); 3.71-3.58 (m, 2H). |
A742072[ 112022-81-8 ]
(S)-1-Methyl-3,3-diphenylhexahydropyrrolo[1,2-c][1,3,2]oxazaborole
Reason: Optical isomers
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