Morpholine → benzyl 2(R)-(4-methoxybenzyl)-3-(morpholinocarbonyl)propionate
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C@H:10]([CH2:10][C:11]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:12])[C:11]([O:13][CH2:9][C:6]2[CH:7]=[CH:8][CH:3]=[CH:4][CH:5]=2)=[O:12])=[CH:7][CH:8]=1Participants
3
Procedure
A procedure similar to those described in Preparations 12-14 was repeated, but using 3-(4-methoxyphenyl)propionic acid as one of the starting materials and morpholine as the amine, to afford benzyl 2(R)-(4-methoxybenzyl)-3-(morpholinocarbonyl)propionate. 1.62 g (4.08 mmole) of this compound was dissolved in 50 ml of ethanol, and the solution was stirred at room temperature for 4 hours under an atmosphere of hydrogen and in the presence of 160 mg of 10% w/w palladium-on-charcoal. At the end of this time, the catalyst was removed by filtration and the filtrate was concentrated by distillation under reduced pressure, to afford 1.25 g of the title compound as a colorless oily substance.
Sources & evidence
- ORD record
- ord-2f7d008015d643d2b68dc310f5a48e6d
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378689
Reaction notes
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