Hydrochloric Acid → HCID 89726298, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (3.0 g, 16 mmol) in dry dimethylformamide at 0° C. was added sodium hexamethyldisilazide (3.5 g, 19 mmol) and after stirring for 5 min cyclopropylmethyl bromide (2.38 g, 17.6 mmol) was added and the mixture was stirred for 40 min at 0° C., then at room temperature for 3 h. After further addition of 1.5 g sodium hexamethyldisilazide and 1.4 g cyclopropylmethyl bromide the mixture was heated at 100° C. for 1 h. After addition of aqueous sodium hydrogencarbonate, the mixture was extracted 3 times with dichloromethane, the solvents were evaporated and the crude mixture was dissolved in dichloromethane (20 ml) and 4 M hydrogen chloride in dioxane (42 ml, 168 mmol). After addition of aqueous hydrochloric acid the organic layer was discarded and the aqueous layer was freeze-dried to give 2.89 g of crude (S)-3-cyclopropylmethoxy-pyrrolidine hydrochloride which was used in the next step without further purification. LC/MS (method 7): Rt=0.34 min; m/z=142.1 (M+H+).

Provenance & Evidence