(8aR)-2-[1-(diphenylmethyl)azetidin-3-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one → (8aR)-2-azetidin-3-ylhexahydropyrrolo[1,2-a]pyrazin-6(2H)-one
Reaction equation
C1(C(C2C=CC=CC=2)[N:8]2[CH2:11][CH:10]([N:12]3[CH2:17][CH2:16][N:15]4[C:18](=[O:21])[CH2:19][CH2:20][C@@H:14]4[CH2:13]3)[CH2:9]2)C=CC=CC=1>C(O)(=O)C.[OH-].[OH-].[Pd+2]>[NH:8]1[CH2:9][CH:10]([N:12]2[CH2:17][CH2:16][N:15]3[C:18](=[O:21])[CH2:19][CH2:20][C@@H:14]3[CH2:13]2)[CH2:11]1Participants
Procedure
(8aR)-2-[1-(diphenylmethyl)azetidin-3-yl]hexahydropyrrolo[1,2-a]pyrazin-6(2H)-one (0.23 g, 0.64 mmol) was dissolved in acetic acid (20 mL) and to the resultant solution was added palladium hydroxide on carbon (0.33 g). The mixture was stirred under hydrogen (5 bar) at RT for 48 h and then the catalyst was filtered off by means of Celite®. The solvent was removed by evaporation and the residue was dissolved in ethanol. The solution was filtered through a cation exchange column (Isolute SCX-2, 10 g). The column was washed with ethanol and then the product was eluted with ammonia-saturated methanol. The solvent was removed by evaporation and there was obtained 0.10 g (84%) of the title compound. 1H NMR (500 MHz, CDCl3): 1.5-1.6 (m, 2H), 1.8 (m, 1H), 2.1-2.2 (m, 1H), 2.3-2.4 (m, 2H), 2.7 (d, 1H), 2.8-2.9 (m, 2H), 3.2 (qn, 1H), 3.5-3.7 (m, 4H), 4.0 (dd, 1H).
Workup
- filtrationthe catalyst was filtered off by means of Celite®
- customThe solvent was removed by evaporation
- dissolutionthe residue was dissolved in ethanol
- filtrationThe solution was filtered through a cation exchange column (Isolute SCX-2, 10 g)
- washThe column was washed with ethanol
- washthe product was eluted with ammonia-saturated methanol
- customThe solvent was removed by evaporation
Sources & evidence
- ORD record
- ord-1eab930ad2684cf283ab5e7771d28659
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08288370B2
Reaction notes
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