Trifluoroacetic acid → (+/-)-Phenylmethyl {[cis-4-fluoro-3-pyrrolidinyl]methyl}carbamate

HRID 639097Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639097
[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]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 15264167Carbonic acid--N,N-diethylethanamine (1/2)HCID 86616800(+/-)-1,1-Dimethylethyl trans-3-fluoro-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate

Produkt 1

HCID 86616799(+/-)-Phenylmethyl {[cis-4-fluoro-3-pyrrolidinyl]methyl}carbamateAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (±)-1,1-dimethylethyl trans-3-fluoro-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (1.0 g, 2.84 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 (11.4 mmole, 4.2 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 (0.54 g, 75%) as a light orange oil: LC-MS (ES) m/e 253 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction solution was concentrated under vacuum
  2. waitthe residue placed under high vacuum for 3 hr
  3. dissolutionThe residue was dissolved in DCM (200 mL)
  4. waitAfter 4 h
  5. customthe reaction contents
  6. filtrationwere filtered through a scintered-glass funnel
  7. washwashing with MeOH (100 mL)
  8. concentrationThe filtrate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e25108ca735846d58c8d29d8c5ef17e8
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

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