N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine → (r)-2-(3-(2-(4-Pyridinyl)ethyl)benzyl)morpholine

Participants

Reaction Steps

Intermediate (a) N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine (43 mg) was dissolved in ethanol (10 mL) with palladium (10% w/w on charcoal, 5 mg) and stirred at room temperature under a hydrogen atmosphere for 4.5 hrs. The reaction mixture was filtered and concentrated in vacuo. The residue (39 mg) was stirred in TFA (20% v/v in dichloromethane, 1.25 mL) at room temperature for 4 hrs. The reaction was poured onto an SCX-2 column (2 g) and washed with dichloromethane (2 mL×2) and methanol (2 mL×2). The SCX-2 column was then washed with ammonia (2N in methanol, 3×2 mL). Combined ammonia washes were concentrated in vacuo to yield the desired morpholine example 31 as a yellow oil (23.5 mg).

Provenance & Evidence