Hydrochloric Acid → 219660-75-0

Participants

Reaction Conditions

Reaction Steps

LDA (14.66 mmol) was generated at 0° C. by adding n-BuLi (6.4 mL of 2.3 M solution in hexane, 14.66 mmol) to a solution of diisopropylamine (2.27 mL, 16.0 mmol) in dry tetrahydrofuran (THF) (13 mL). N-(diphenylmethylidene)-3-(aminomethyl)pyridine (3.62 g, 13.33 mmol) was dissolved in dry tetrahydrofuran (13 mL) and the solution cooled to −78° C. under a nitrogen atmosphere. LDA was then transferred to the solution of N-(diphenylmethylidene)-3-(aminomethyl)pyridine using a double tipped needle under a positive nitrogen atmosphere. The resulting purple suspension was stirred for a further 45 minutes, during which time the temperature of the reaction mixture was allowed to rise to −4° C. Tetrahydro-3-furanmethanol methanesulfonate (2.64 g, 14.7 mmol) in tetrahydrofuran (10 mL) was then added via a syringe and the reaction mixture was allowed to warm to ambient temperature followed by additional stirring for 12 hours. Hydrochloric acid (10% aq., 20 mL) was added, and the reaction mixture was stirred for 20-30 minutes followed by extraction with ethyl acetate (3×25 mL). The resulting aqueous solution was first made basic by adding solid K2CO3, and then extracted with chloroform (3×25 mL). The combined organic extracts were dried over anhydrous K2CO3. Filtration was followed by evaporation of chloroform to yield 1-amino-1-(3-pyridyl)-2-(3-tetrahydrofuranyl)-ethane as a diastereomeric (50:50) mixture (pale yellow oil, 2.03 g) which was used in the next step without further purification.

Provenance & Evidence