N-Boc-(R)-2-(3-(2-(4-pyridinyl)vinyl)-benzyl)morpholine → (r)-2-(3-(2-(4-Pyridinyl)ethyl)benzyl)morpholine
Reaction equation
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[CH:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[CH:16]=2)[CH2:9]1)(OC(C)(C)C)=O>C(O)C.[Pd]>[N:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C:17]2[CH:16]=[C:15]([CH:20]=[CH:19][CH:18]=2)[CH2:14][C@H:10]2[O:11][CH2:12][CH2:13][NH:8][CH2:9]2)=[CH:24][CH:25]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
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).
Workup
- filtrationThe reaction mixture was filtered
- concentrationconcentrated in vacuo
- stirringThe residue (39 mg) was stirred in TFA (20% v/v in dichloromethane, 1.25 mL) at room temperature for 4 hrs
- additionThe reaction was poured onto an SCX-2 column (2 g)
- washwashed with dichloromethane (2 mL×2) and methanol (2 mL×2)
- washThe SCX-2 column was then washed with ammonia (2N in methanol, 3×2 mL)
- concentrationCombined ammonia washes were concentrated in vacuo
Sources & evidence
- ORD record
- ord-ecfb5750a5754b63bac50352cb4bd24a
- Source dataset
- uspto-grants-2008_01
- Patent number
- US07323466B2
Reaction notes
Loading…