4-Phenylpiperidine → 3-(4-Phenyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][C:22](=O)[CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[C:13]([O:17][C:18]([N:20]1[CH2:24][CH2:23][CH:22]([N:10]2[CH2:9][CH2:8][CH:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:12][CH2:11]2)[CH2:21]1)=[O:19])([CH3:16])([CH3:14])[CH3:15]Participants
Procedure
To a suspension of 4-phenylpiperidine (2.12 g, 13.1 mmol) and 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (2.43 g, 13.1 mmol) in MeOH (60 mL) was added NaBH(OAc)3 (8.32 g, 39.3 mmol) and the reaction mixture was stirred at ambient temperature for about 16 h. The reaction mixture was concentrated in vacuo. The residue was dissolved in DCM (50 mL) and stirred with saturated aqueous NaHCO3 (50 mL) for about 1 h. The organic portion was separated, dried over MgSO4, filtered, and concentrated in vacuo to give 3-(4-phenyl-piperidin-1-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (4.3 g,) as a yellow oil which was used in subsequent reactions without further purification. RP-HPLC (Table 1, Method d) Rt 2.73 min; m/z: (M+H)+ 331.
Workup
- concentrationThe reaction mixture was concentrated in vacuo
- dissolutionThe residue was dissolved in DCM (50 mL)
- stirringstirred with saturated aqueous NaHCO3 (50 mL) for about 1 h
- customThe organic portion was separated
- dry with materialdried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e4bdf59cefae44d19e6c3f99b6331bc4
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08754107B2
Reaction notes
Loading…