Benzaldehyde → tert-Butyl 4-(benzyl(methyl)amino)piperidine-1-carboxylate
Reaction equation
[CH3:1][NH:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[CH:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:16]([N:2]([CH3:1])[CH:3]1[CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])[CH2:7][CH2:8]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1Participants
5
Procedure
tert-Butyl 4-(methylamino)piperidine-1-carboxylate (3.0 g, 14.019 mmol, 1.0 eq.) was dissolved in DCM (30 ml); benzaldehyde (1.7 ml, 16.823 mmol, 1.2 eq.) was added and the mixture was stirred for 1 hour at RT. NaBH(OAc)3 (4.81 g, 28.038 mmol, 3.0 eq.) was then added at 0° C. and the reaction mixture was stirred for 14 hours at RT. After monitoring by TLC, DCM (300 ml) was added to the reaction and washing was carried out in succession with sodium hydrogen carbonate solution (100 ml), water (100 ml) and sat. NaCl solution (100 ml). The organic phase was dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 1% MeOH in DCM). Yield: 28% (1.2 g, 3.947 mmol)
Workup
- stirringthe reaction mixture was stirred for 14 hours at RT
- additionwas added to the reaction
- washwashing
- dry with materialThe organic phase was dried over sodium sulfate
- concentrationconcentrated under reduced pressure
- custompurified by column chromatography (silica gel, 1% MeOH in DCM)
Sources & evidence
- ORD record
- ord-33583f16ce7c4a8ba482ca0ab770aa3c
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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