Cyclopropylamine → tert-Butyl (3S,4S)-3-((cyclopropylamino)methyl)-4-fluoropyrrolidine-1-carboxylate
Reaction equation
Br[CH2:2][C@@H:3]1[C@H:7]([F:8])[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[CH:16]1([NH2:19])[CH2:18][CH2:17]1>>[C:12]([O:11][C:9]([N:5]1[CH2:6][C@@H:7]([F:8])[C@@H:3]([CH2:2][NH:19][CH:16]2[CH2:18][CH2:17]2)[CH2:4]1)=[O:10])([CH3:15])([CH3:14])[CH3:13]Participants
3
Conditions
- Temperature
- 80 °C
Procedure
(3S,4S)-3-Bromomethyl-1-tert-butoxycarbonyl-4-fluoropyrrolidine (1.91 g) was mixed with cyclopropylamine (23.6 mL). The mixture was stirred at 80° C. for 23 hours and was concentrated under reduced pressure. The residue was dissolved in ethyl acetate (100 mL), washed with saturated brine (2×20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1) to give (3S,4S)-1-tert-butoxycarbonyl-3-cyclopropylaminomethyl-4-fluoropyrrolidine as a pale brown oil (1.67 g).
Workup
- concentrationwas concentrated under reduced pressure
- dissolutionThe residue was dissolved in ethyl acetate (100 mL)
- washwashed with saturated brine (2×20 mL)
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under reduced pressure
- customThe resulting residue was purified by silica gel column chromatography (eluant: hexane: ethyl acetate=2:1)
Sources & evidence
- ORD record
- ord-fda1f95a9e254eacb89d08e41211933b
- Source dataset
- uspto-grants-2009_04
- Patent number
- US07514451B2
Reaction notes
Loading…