Benzyl 4-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine-1-carboxylate → 1-[((3R)-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][C@@H:16]([CH2:20][N:21]3[CH2:26][CH2:25][N:24](C(OCC4C=CC=CC=4)=O)[CH2:23][CH2:22]3)[CH2:15]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]>CO>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:11][CH2:12][CH2:13][N:14]2[CH2:19][CH2:18][CH2:17][C@@H:16]([CH2:20][N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH2:15]2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]Participants
3
Procedure
Benzyl 4-[((3R)-1-{3-[4-(methylsulfonyl)phenyl]propyl}piperidin-3-yl)methyl]piperazine-1-carboxylate (5.00 g, 9.70 mmol) was dissolved in methanol (30 ml) in a three-necked flask. The air was removed under reduced pressure and replaced with argon before the addition of 10% Pd/C (1.00 g). A balloon of hydrogen was then added and the reaction stirred at room temperature for 18 h. The hydrogen was evacuated and replaced with argon. The catalyst was then filtered using a nylon whatman autocup and the solvent removed under reduced pressure to afford the desired product as a yellow gum (3.50 g, 95% crude yield).
Workup
- customThe air was removed under reduced pressure
- additionreplaced with argon before the addition of 10% Pd/C (1.00 g)
- additionA balloon of hydrogen was then added
- customThe hydrogen was evacuated
- filtrationThe catalyst was then filtered
- customthe solvent removed under reduced pressure
Sources & evidence
- ORD record
- ord-299b01b9338e4e079506883cfa7aea72
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07906645B2
Reaction notes
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