2-methoxy-2-methylpropanoyl chloride

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 295 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol in 6.6 mL of DCM was added 1.4 mL of NEt3, 81 mg of DMAP and 0.8 mL of 2-methoxy-2-methyl propanoyl chloride (prepared as in JOC, 1976, 41, 19, 3182-3187) at 0° C. The reaction mixture was allowed to warm up to rt and stirred for 5 min at rt before 0.3 mL of anh. THF was added. The reaction mixture was stirred overnight at 50° C., extracted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The crude product was purified by CC using DCM/MeOH/DIPEA 95/5/1 to yield 214 mg of rac-2-methoxy-2-methyl-propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as white foam. was added extracted with DCM washed with sat. NaHCO3 The organic phase was dried over anh. Na2SO4 concentrated in vacuo The crude product was purified by CC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 295 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol in 6.6 mL of DCM was added 1.4 mL of NEt3, 81 mg of DMAP and 0.8 mL of 2-methoxy-2-methyl propanoyl chloride (prepared as in JOC, 1976, 41, 19, 3182-3187) at 0° C. The reaction mixture was allowed to warm up to rt and stirred for 5 min at rt before 0.3 mL of anh. THF was added. The reaction mixture was stirred overnight at 50° C., extracted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The crude product was purified by CC using DCM/MeOH/DIPEA 95/5/1 to yield 214 mg of rac-2-methoxy-2-methyl-propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as white foam. was added extracted with DCM washed with sat. NaHCO3 The organic phase was dried over anh. Na2SO4 concentrated in vacuo The crude product was purified by CC

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 295 mg of rac-(1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-ol in 6.6 mL of DCM was added 1.4 mL of NEt3, 81 mg of DMAP and 0.8 mL of 2-methoxy-2-methyl propanoyl chloride (prepared as in JOC, 1976, 41, 19, 3182-3187) at 0° C. The reaction mixture was allowed to warm up to rt and stirred for 5 min at rt before 0.3 mL of anh. THF was added. The reaction mixture was stirred overnight at 50° C., extracted with DCM and washed with sat. NaHCO3. The organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The crude product was purified by CC using DCM/MeOH/DIPEA 95/5/1 to yield 214 mg of rac-2-methoxy-2-methyl-propionic acid (1R*,2R*,4R*)-2-(2-{[3-(4-methoxy-1H-benzoimidazol-2-yl)-propyl]-methyl-amino}-ethyl)-5-phenyl-bicyclo[2.2.2]oct-5-en-2-yl ester as white foam. was added extracted with DCM washed with sat. NaHCO3 The organic phase was dried over anh. Na2SO4 concentrated in vacuo The crude product was purified by CC