Toluene → 2,2-dimethylpropionic acid 2-((S)-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-((S)-3-tert-butoxycarbonylaminopiperidin-1-yl)ethyl ester (2.54 g, 7.73 mmol) in DCM (80 mL) was added TFA (20 mL) and the mixture was stirred at RT for 2 h. Toluene was added and volatiles 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 was eluted with 1M NH3/MeOH. The product containing fractions were combined and concentrated in vacuo affording the title compound as a pale yellow oil (1.567 g, 89%). 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), 2.20-2.12 (1H, m), 2.00-1.94 (1H, m), 1.82-1.65 (2H, m), 1.60-1.46 (1H, m), 1.28 (2H, bs), 1.20 (9H, s), 1.15-1.03 (1H, m).
Workup
- customvolatiles removed in vacuo
- dissolutionThe resulting residue was dissolved in MeOH
- washThe cartridge was washed with MeOH
- washthe product was eluted with 1M NH3/MeOH
- additionThe product containing fractions
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-fc5d881a99bb4ff4a21cc9e8b4bc964c
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08653089B2
Reaction notes
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