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US 11,958,818 B2Granted
(R)-(2-methyloxiran-2-yl)methyl 4-bromobenzenesulfonate
AssigneeBoehringer Ingelheim International GmbH
InventorNitinchandra D. Patel
Life of this patent
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Abstract
The present invention relates to compound of formula (I), wherein R1 is chloro, bromo iodo or a brosylate group. The present invention also relates to methods of making this compound and its use in carrying out organic transformations.
Claims11
A process for making Compound 1:
- the process comprising:
- (i) contacting an admixture comprising methylallyl alcohol, (+)-di-isopropyl L-tartrate (L-DIPT) and a solvent/diluent with molecular sieves to provide a first anhydrous admixture;
- (ii) cooling the first anhydrous admixture;
- (iii) adding Ti(O-iPr)4 to the cooled anhydrous admixture in step (ii) to provide a second anhydrous admixture;
- (iv) adding cumene hydroperoxide to the second anhydrous admixture of step (iii) to provide a first reaction mixture;
- (v) allowing the contents of the first reaction mixture to react to provide an admixture comprising INT-1;
- (vi) filtering the admixture obtained from step (v) to provide a filtrate comprising INT-1;
- (vii) optionally treating the filtrate obtained from step (vi) with trimethylphosphite to quench unreacted cumene hydroperoxide (“the quenched filtrate”);
- and
- (viii) treating the filtrate from step (vi) or the optionally quenched filtrate of step (vii) with triethylamine (Et3N), 4-dimethylaminopyridine (DMAP), and 4-bromobenzene-1-sulfonyl chloride (BrsCl) to provide a second reaction mixture;
- and
- (ix) allowing the contents of the second reaction mixture to react to provide an admixture comprising Compound 1.
9 more elements
A process for making Compound 1
- the process comprising:
- (i) carrying out an azeotropic distillation of solution comprising cumene hydroperoxide and a solvent capable of forming an azeotrope to provide a first anhydrous solution;
- (ii) cooling the first anhydrous solution;
- (iii) carrying out an azeotropic distillation of a solution comprising methylallyl alcohol, (+)-di-isopropyl L-tartrate (L-DIPT), and a solvent capable of forming an azeotrope to provide a second anhydrous solution;
- (iv) cooling the second anhydrous solution;
- (v) adding titanium tetraisoproxide (Ti(O-iPr)4) to the cooled second anhydrous solution in step (iv);
- (vi) combining the cooled first solution from step (ii) with the cooled second anhydrous solution from step (v) to provide a first reaction solution;
- (vii) allowing the contents of the first reaction solution from step (vi) to react to provide a solution comprising INT-1;
- (viii) optionally treating the solution obtained from step (vii) with trimethylphosphite to quench unreacted cumene hydroperoxide;
- and
- (ix) treating the solution obtained from step (vii), or the optionally quenched solution of step (viii), with triethylamine (Et3N), 4-dimethylaminopyridine (DMAP), and 4-bromobenzene-1-sulfonyl chloride (BrsCl) to provide a reaction solution comprising Compound 1.
8 more elements
A process for making the compound of formula I
- wherein R1 is chloro, bromo, or iodo,
- the process comprising reacting Compound 1 of formula:
- with a tetraethylammonium halide of formula (CH3CH2)4N+X− in a suitable diluent/solvent,
- wherein X is chloro, bromo, or iodo.
1 more element
Dependencies are inferred from the claim text.