Trifluoroacetic acid → Racemic 4-{[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-one

HRID 15359Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15359
CC([N:5]([C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([F:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][C@@H:10]1[OH:30])C(=O)[O-])(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:5][C@@H:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH:16]2[C:20]3=[C:21]([F:29])[CH:22]=[N:23][C:24]4[CH:25]=[CH:26][C:27](=[O:28])[N:18]([C:19]=43)[CH2:17]2)[CH2:11][C@@H:10]1[OH:30]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 131728174HCID 131728174, Verbindung

Produkt 1

HCID 68684481Racemic 4-{[(3S,4R)-4-amino-3-hydroxy-1-piperidinyl]methyl}-3-fluoro-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-7-oneAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of racemic 1,1-dimethylethyl{(3S,4R)-1-[(3-fluoro-7-oxo-4,5-dihydro-7H-pyrrolo[3,2,1-de]-1,5-naphthyridin-4-yl)methyl]-3-hydroxy-4-piperidinyl}carbamate (15.57 g) in dichloromethane (170 ml) was cooled in ice-water, treated with trifluoracetic acid (137 ml), stirred 1 hour at room temperature and evaporated to dryness. After keeping under high vacuum for 1 hour, the crude material was dissolved in methanol and run through a column of Amberlyst A21 basic resin (500 ml) (Sigma-Aldrich Co.), eluting with methanol. The solution containing the product was evaporated and the residue chromatographed on silica gel, eluting with dichloromethane/methanol/0.88 ammonia (9:1:0.1) to give product (8.96 g, 76%).

Aufarbeitung

  1. customevaporated to dryness
  2. waitAfter keeping under high vacuum for 1 hour
  3. dissolutionthe crude material was dissolved in methanol
  4. washeluting with methanol
  5. additionThe solution containing the product
  6. customwas evaporated
  7. customthe residue chromatographed on silica gel
  8. washeluting with dichloromethane/methanol/0.88 ammonia (9:1:0.1)

Quellen und Nachweise

ORD-Eintrag
ord-5227c8331d0b4dce93bf2739e19ce181
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732461B2

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