Trifluoroacetic acid → (+/-)-Phenylmethyl {[cis-4-fluoro-3-pyrrolidinyl]methyl}carbamate
Reaktionsgleichung
[F:1][C@H:2]1[C@@H:6]([CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.C(O)(C(F)(F)F)=O.CC[NH+](CC)CC.CC[NH+](CC)CC.C([O-])([O-])=O>C(Cl)Cl>[F:1][C@H:2]1[CH2:3][NH:4][CH2:5][C@H:6]1[CH2:7][NH:8][C:9](=[O:10])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Versuchsvorschrift
To a solution of (±)-1,1-dimethylethyl cis-3-fluoro-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (0.45 g, 1.28 mmole) in DCM (50 mL) at RT was added TFA (25 mL). After 2 h, the reaction solution was concentrated under vacuum and the residue placed under high vacuum for 3 hr. The residue was dissolved in DCM (200 mL) and MP-carbonate resin (5.12 mmole, 1.9 g) was added with vigorous stirring at RT. After 4 h, the reaction contents were filtered through a scintered-glass funnel washing with MeOH (100 mL). The filtrate was concentrated under vacuum to give the title compound (0.32 g, 99%) as a light orange oil: LC-MS (ES) m/e 253 (M+H)+.
Aufarbeitung
- concentrationthe reaction solution was concentrated under vacuum
- waitthe residue placed under high vacuum for 3 hr
- dissolutionThe residue was dissolved in DCM (200 mL)
- waitAfter 4 h
- customthe reaction contents
- filtrationwere filtered through a scintered-glass funnel
- washwashing with MeOH (100 mL)
- concentrationThe filtrate was concentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-1546abf94dda42e5b27207a7d55e4eab
- Quelldatensatz
- uspto-grants-2010_04
- Patentnummer
- US07691850B2
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