Acetic Acid → N-Benzylcytisine

HRID 986921

Reaktionsgleichung

Reaktionsgleichung von HRID 986921
[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][NH:4][CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]1[C@H:6]2[C:7]3[N:13]([CH2:14][C@@H:2]1[CH2:3][N:4]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:5]2)[C:11](=[O:12])[CH:10]=[CH:9][CH:8]=3

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 240BenzaldehydeHCID 10235CytisineHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 872912N-BenzylcytisineAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

To a 25 ml round bottom flask was added 0.510 gm (2.68 mmol) cytisine in 10 ml of 1,2-dichloroethane. The above solution was treated with 0.272 ml (2.68 mmol) benzaldehyde, 153 μl acetic acid and 0.852 gm (4.02 mmol) sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 hours and was then partitioned between methylene chloride 1 N HCl (aq). The organic phase was washed with brine, dried and the solvent evaporated in vacuo to a solid. Chromatography on silica gel eluting with 1% methanol in methylene chloride afforded 434 mg (58%) of the title product which was used in the next step. 1H NMR (CDCl3, 250 MHz) δ7.28 (dd, 1H), 7.15 (m, 3H), 6.98 (m, 2H), 6.52 (d, 1H), 5.92 (d, 1H), 4.10 (d, 1H), 3.88 (dd, 1H), 3.40 (dd, 2H), 2.88 (m 3H), 2.39 (brs, 1H), 2.32 (dd, 2H), 1.82 (dd, 2H) ppm.

Aufarbeitung

  1. customwas then partitioned between methylene chloride 1 N HCl (aq)
  2. washThe organic phase was washed with brine
  3. customdried
  4. customthe solvent evaporated in vacuo to a solid

Quellen und Nachweise

ORD-Eintrag
ord-cdad4cd2fa6843b5ad294d5cb3bf27f9
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630467B2

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