N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine → (R)-2-(3-(2-(3-pyridinyl)ethyl)benzyl)morpholine

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Reaction Steps

N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine intermediate (a) was dissolved in ethanol (8 mL), with palladium on charcoal (10% w/w, 5 mg) and stirred at room temperature under an atmosphere of hydrogen (1 balloon containing hydrogen) for 18 hours. The reaction was filtered through a pad of celite, washing with ethanol, and the solution was concentrated in vacuo. The crude material was used in the next step without further purification. N-Boc-(R)-2-(3-(2-(3-pyridinyl)ethyl)-benzyl)morpholine (25 mg), was dissolved in a solution of TFA in dichloromethane (20% v/v, 1 mL total) and stirred at room temperature for 3 hrs. The reaction was then poured through an SCX-2 column and washed with dichloromethane. The column was then washed with ammonia (2N, methanol) and the ammonia washes concentrated in vacuo. The residue was purified by column chromatography (prepacked silica, 1 g; dichloromethane/methanol/ammonium hydroxide, 100:10:1) to obtain the desired product example 48 (R)-2-(3-(2-(3-pyridinyl)ethyl)benzyl)morpholine as a yellow oil (10 mg).

Provenance & Evidence