Acetic Acid → (R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

HRID 1738323Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1738323
[NH2:1][C@@H:2]1[CH2:7][C:6]2[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([F:12])[C:5]=2[O:4][CH2:3]1.[C:15]1(=O)[CH2:19][CH2:18][CH2:17][CH2:16]1.CC(O)=O.[BH3-]C#N.[Na+]>CO>[CH:15]1([NH:1][C@@H:2]2[CH2:7][C:6]3[C:8]([O:13][CH3:14])=[CH:9][CH:10]=[C:11]([F:12])[C:5]=3[O:4][CH2:3]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8452CyclopentanoneHCID 5003444Sodium cyanoborohydrideHCID 22871215(R)-8-fluoro-5-methoxy-3-aminochroman

Produkt 1

HCID 22871220(R)-3-(N-cyclopentylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (R)-3-amino-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran (2.5 g, 12 mmol), cyclopentanone (3.3 g, 36 mmol) and HOAc (0.7 g, 12 mmol) in methanol (25 mL) was NaCNBH3 (2.5 g, 40 mmol) added in portions at room temperature. The solution was stirred at room temperature overnight to give a quantitative yield of the title compound. GC/MS (70 eV) M=265 (30%).

Aufarbeitung

  1. additionadded in portions at room temperature

Quellen und Nachweise

ORD-Eintrag
ord-e1dd31dd3b4541acb6170b7cbb842a41
Quelldatensatz
uspto-grants-1999_10
Patentnummer
US05962514

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