Acetic Acid → HCID 22871221, Verbindung

HRID 1738329Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1738329
[CH:1]1([NH:6][C@@H:7]2[CH2:12][C:11]3[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[O:9][CH2:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CC(O)=O.[C:24]1(=O)[CH2:27][CH2:26][CH2:25]1.[BH3-]C#N.[Na+]>CO>[CH:1]1([N:6]([C@@H:7]2[CH2:12][C:11]3[C:13]([O:18][CH3:19])=[CH:14][CH:15]=[C:16]([F:17])[C:10]=3[O:9][CH2:8]2)[CH:24]2[CH2:27][CH2:26][CH2:25]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

6

Edukt 4

HCID 176Acetic Acid2×HCID 14496Cyclobutanone2×HCID 5003444Sodium cyanoborohydrideHCID 22871220(R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

Produkt 1

HCID 22871221HCID 22871221, VerbindungAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (0.9 g, 3.4 mmol), HOAc (0.22 g, 3.6 mmol) and cyclobutanone (2g, 30 mmol) in methanol (25 mL), were NaCNBH3 (1 g, 16 mmol) added in portions at room temperature. After stirring for four days GC indicated 37% product. pH was adjusted to 5 (HOAc) and additional (1 g, 15 mmol) cyclobutanone was added. After stirring for further 6 days, GC indicated 64% conversion. The solvent was evaporated and the residue worked up by extraction. Flash chromatography (EtOAc/P-ether, 1+1), gave 0.53 g (53% yield) of the title compound as a colourless oil. GC/MS (70 eV) M=319 (3%).

Aufarbeitung

  1. additionadded in portions at room temperature
  2. additionwas added
  3. customThe solvent was evaporated
  4. extractionthe residue worked up by extraction

Quellen und Nachweise

ORD-Eintrag
ord-efcaef69a86f40a9993f7fbb5adafefb
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962514

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