tert-Butyl 4-oxopiperidine-1-carboxylate → 4-[4-(4-Chloro-phenyl)-3-oxo-5-pyridin-4-yl-pyrazolidin-1-yl]-piperidine-1-carboxylic acid tert-butyl ester
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[NH:11][NH:10][C:9]2=[O:19])=[CH:4][CH:3]=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>C(Cl)(Cl)Cl>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([N:11]2[CH:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[CH:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[C:9](=[O:19])[NH:10]2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 4-(4-Chloro-phenyl)-5-pyridin-4-yl-pyrazolidin-3-one 0.86 g and 4-Oxo-piperidine-1-carboxylic acid tert-butyl ester 0.75 g in chloroform 35 mL was added sodium triacetoxy boron hydride 0.75 g at 0° C., the reaction was warmed up to room temperature over two hours before heated to 50° C. for another two hours. The reaction was quenched with water 25 mL at 0° C., and the organic layer was collected, filtered, dried over MgSO4, concentrated to a yellow solid 0.42 g for being directly used for next step. MS (ES+): 457 (M+H)+.
Workup
- temperaturebefore heated to 50° C. for another two hours
- customThe reaction was quenched with water 25 mL at 0° C.
- customthe organic layer was collected
- filtrationfiltered
- dry with materialdried over MgSO4
- concentrationconcentrated to a yellow solid 0.42 g
Sources & evidence
- ORD record
- ord-8e821cbe684a495cb807d7c7bed869bf
- Source dataset
- uspto-grants-2005_11
- Patent number
- US06967254B2
Reaction notes
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