Trifluoroacetic acid → Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamate

HRID 639065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639065
[OH: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>[OH: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 59254350rac-tert-butyl (3R,4R)-3-({[(benzyloxy)carbonyl]amino}methyl)-4-hydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 86616784Phenylmethyl {[(3S,4R)-4-hydroxy-3-pyrrolidinyl]methyl}carbamateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (±)-1,1-dimethylethyl cis-3-hydroxy-4-[({[(phenylmethyl)oxy]carbonyl}amino)methyl]-1-pyrrolidinecarboxylate (15.3 g, 43.7 mmole) in DCM (150 mL) at RT was added TFA (50 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 (175 mmole, 65 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 (10.38 g, 95%) as a white foam: LC-MS (ES) m/e 251 (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-c6d72899091846dcb084c4c742e7d864
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691850B2

Notizen zur Reaktion

Wird geladen…