Sodium Bicarbonate → 2,2,2-trifluoro-1-(7-hydroxy-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)ethanone

HRID 2187573Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2187573
[F:1][C:2]([F:22])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([O:17]C(=O)C)=[CH:12][C:13]=32)[CH2:6]1)=[O:4].C([O-])(O)=O.[Na+]>CO>[F:22][C:2]([F:1])([F:21])[C:3]([N:5]1[CH2:15][CH:14]2[CH2:16][CH:7]([C:8]3[CH:9]=[CH:10][C:11]([OH:17])=[CH:12][C:13]=32)[CH2:6]1)=[O:4]

Komponenten

4

Edukt 2

HCID 516892Sodium BicarbonateHCID 54458016Acetic acid 10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl ester

Produkt 1

HCID 218647432,2,2-trifluoro-1-(7-hydroxy-4,5-dihydro-1H-1,5-methanobenzo[d]azepin-3(2H)-yl)ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Acetic acid 10-trifluoroacetyl-10-aza-tricyclo[6.3.1.02,7]dodeca-2(7),3,5-trien-4-yl ester (900 mg, 2.87 mmol) was stirred in MeOH (20 mL) and saturated aqueous NaHCO3 solution (15 mL) for 48 hours. The mixture was concentrated, diluted with H2O and extracted with CH2Cl2 (3×20 mL) then dried through a cotton plug. Chromatography on Silica gel provided pure product (420 mg, 54%). (TLC 5% MeOH/CH2Cl2 Rf 0.44). 1H NMR (400 MHz, CDCl3) δ7.05 (m, 1H), 6.70 (m, 1H), 6.62 (m, 1H), 4.32 (m, 1H), 3.84 (m, 1H), 3.48 (m, 1H), 3.21 (br s, 1H), 3.16 (br s, 1H), 3.09 (m, 1H), 2.38 (m, 1H), 1.97 (d, J=11.0 Hz, 1H).

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. additiondiluted with H2O
  3. extractionextracted with CH2Cl2 (3×20 mL)
  4. customthen dried through a cotton plug

Quellen und Nachweise

ORD-Eintrag
ord-6023453e7bb3435084d824496fc77df8
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06410550B1

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