Toluene → 2,2-Dimethylpropionic acid 2-((R)-3-aminopiperidin-1-yl)ethyl ester
Reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:10]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH2:15][CH2:16][O:17][C:18](=[O:23])[C:19]([CH3:21])([CH3:20])[CH3:22])[CH2:10]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice-cooled solution of 2,2-dimethylpropionic acid 2-((R)-3-tert-butoxycarbonylaminopiperidin-1-yl)ethyl ester (2.86 g, 8.72 mmol) in DCM (100 mL) was added TFA (25 mL) and the mixture stirred at RT for 3 h. Toluene was added and volatiles were removed in vacuo. The resulting residue was dissolved in MeOH and loaded onto an Isolute® SCX-2 cartridge. The cartridge was washed with MeOH and the product eluted with 1M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a colourless oil (1.678 g, 84%). 1H NMR (CDCl3, 300 MHz): 4.18 (2H, t, J=6.0 Hz), 2.89-2.77 (2H, m), 2.68-2.59 & 2.62 (3H, m & t, J=6.0 Hz), 2.19-2.11 (1H, m), 2.00-1.94 (1H, m), 1.84-1.65 (2H, m), 1.60-1.46 (1H, m), 1.23 (2H, bs), 1.20 (9H, s), 1.15-1.03 (1H, m).
Workup
- customvolatiles were removed in vacuo
- dissolutionThe resulting residue was dissolved in MeOH
- washThe cartridge was washed with MeOH
- washthe product eluted with 1M NH3/MeOH
- additionThe product containing fractions
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b5896fd3af6c4c9e82e6ff527df251a6
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
Loading…