Benzyl (3R,4R)-3-fluoro-4-(3-(methylsulfonyl)propanamido)pyrrolidine-1-carboxylate → N-((3R,4R)-4-fluoropyrrolidin-3-yl)-3-(methylsulfonyl)propanamide
Reaction equation
[F:1][C@H:2]1[C@H:6]([NH:7][C:8](=[O:15])[CH2:9][CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[CH2:5][N:4](C(OCC2C=CC=CC=2)=O)[CH2:3]1>C(O)C.[Pd]>[F:1][C@@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[NH:7][C:8](=[O:15])[CH2:9][CH2:10][S:11]([CH3:14])(=[O:12])=[O:13]Participants
Procedure
A nitrogen sparged suspension of (3R,4R)-benzyl 3-fluoro-4-(3-(methylsulfonyl)propanamido)pyrrolidine-1-carboxylate (2.80 g, 7.52 mmol, 1.00 eq) and 10% Pd/C (300 mg) in ethanol (250 mL) was stirred under a hydrogen atmosphere (1 atm) for 16 hr. The reaction mixture was then sparged with nitrogen and filtered through a pad of Celite®. The Celite® was washed with additional ethanol (50 mL). The combined filtrates were concentrated under reduced pressure to give the title compound (1.75 g, 98% yield, 95% purity) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.13 (d, J=6.7 Hz, 1 H) 4.73-5.02 (m, 1 H) 3.99-4.20 (m, 1 H) 3.32 (t, J=7.6 Hz, 2 H) 3.14 (dd, J=11.7, 6.8 Hz, 2 H) 2.94-3.01 (m, 4 H) 2.87-2.91 (m, 1 H) 2.52-2.59 (m, 3 H). m/z (APCI+) for C8H16FN2O3S 239.2 (M+H)+.
Workup
- customA nitrogen sparged
- customThe reaction mixture was then sparged with nitrogen
- filtrationfiltered through a pad of Celite®
- washThe Celite® was washed with additional ethanol (50 mL)
- concentrationThe combined filtrates were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-461952e95934430db2d54bd280fedbed
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09290496B2
Reaction notes
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