Isopropylamine → rac-isopropyl-carbamic 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

Participants

Reaction Steps

To a solution of 91 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 2 mL of anh. THF were added 57 mg of NaH at −10° C. The suspension was stirred for 45 min allowing the temperature to reach 0° C. 171 mg of 1,1′-carbonyldiimidazole were added at −10° C. and the mixture stirred for 30 min at rt. 0.178 mL of isopropyl amine was added at 0° C. and the reaction mixture stirred overnight at rt. After quenching with sat. NaHCO3 and extracting with DCM, the organic phase was dried over anh. Na2SO4 and concentrated in vacuo. The crude product was purified by prep. TLC using chloroform/MeOH/NEt3 70/30/1 to yield 45 mg of rac-isopropyl-carbamic 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 yellowish oil.

Provenance & Evidence