Acetic Acid → HCID 14371634, Verbindung

HRID 1074165Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1074165
[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4.C=O.[C:24]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[CH3:1][O:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]2[CH2:12][CH2:11][N:10]([CH3:24])[C@@H:9]3[CH2:13][C:14]4[C:19]([C@H:8]3[C:7]=2[CH:20]=1)=[CH:18][CH:17]=[CH:16][CH:15]=4

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 14371630HCID 14371630, Verbindung

Produkt 1

HCID 14371634HCID 14371634, VerbindungAusbeute 47,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A solution of 300 mg (1.00 mmol) of Compound P from step E was dissolved in 20 mL acetonitrile and 0.40 mL (5.3 mmol) 37% aqueous formaldehyde was added followed by 0.10 grams (1.59 mmol) sodium cyanoborohydride. After 30 minutes, the solution was brought to pH 7 by dropwise addition of glacial acetic acid then stirred an additional 1 hour and 45 minutes. The solvent was removed under reduced pressure, and the residue was taken up into 125 mL ethyl acetate. This was washed with 50 mL 10% sodium bicarbonate, dried (MgSO4) and evaporated to give an oil, which was purified by flash chromatography over silica gel, eluting with ethyl acetate to give 150 mg of trans-5,6,7,7a,8,12b-hexahydro-2-methoxy-3-chloro-7-methyl-benz[d]indeno[2,1-b]azepine (Compound Q) as an oil, 200 MHz NMR (CDCl3) d 2.17(dd,1H,J=12,Hz), 2.69(m,2H) 2.37(s,3H), 2.90-3.40(m,4H), 3.77(s,3H), 4.67(d,1H,J=9 Hz), 7.03(s,1H), 7.17(s,1H), 7.20-7.35(m,4H).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. washThis was washed with 50 mL 10% sodium bicarbonate
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oil, which
  6. customwas purified by flash chromatography over silica gel
  7. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-39a808ae22d14c73b0206fa8ce9a4ea0
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04973586

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