Diethyl Ether → cis-1,6-Dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline

HRID 67800Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 67800
CC[O:3][CH2:4][CH3:5].[Na+].[Cl-].C(O[CH2:11][C:12]1[C:13](=[O:27])[N:14]([CH3:26])[CH2:15][CH2:16][C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=1)=O.[CH2:28]1COCC1>>[O:27]=[C:13]1[C@@H:12]2[C@@:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[CH:19]=3)([CH2:28][C:4](=[O:3])[CH2:5][CH2:11]2)[CH2:16][CH2:15][N:14]1[CH3:26]

Komponenten

5

Edukt 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 129475523-Formyloxymethyl-4-(3'-methoxyphenyl)-1-methyl-5,6-dihydro-2-pyridone

Produkt 1

HCID 86736842cis-1,6-Dioxo-4a-(3'-methoxyphenyl)-2-methyldecahydroisoquinoline

Versuchsvorschrift

Ketal cis-34 (Example 16) (20 mg, 0.06 mmol) was dissolved in 1:1 THF/1 N H2SO4 (2 mL) and stirred for 60 h. Ether (2 mL) and saturated NaCl (1 mL) were added, the aqueous phase washed with ether (1 mL), and the combined organic phases washed with saturated NaCl (2 mL), dried, and evaporated to yield 17 mg (99%) of pure cis-9: NMR δ 7.30 (t,J=9 Hz, 1H), 6.9 (m, 3H), 3.78 (s, 3H), 7.87 (s, 3H), 2.63 (s, 2H); IR 1712, 1634, 1603, 1580 cm-1 ; mass spectrum m/e (rel intensity) 287 (32), 218 (26), 55 (100). Anal. Calcd for C17H21NO3 : C, 71.0; H, 7.4; N, 4.9. Found: C, 71.0; H, 7.4; N, 4.9.

Aufarbeitung

  1. washthe aqueous phase washed with ether (1 mL)
  2. washthe combined organic phases washed with saturated NaCl (2 mL)
  3. customdried
  4. customevaporated
  5. customto yield 17 mg (99%) of pure cis-9

Quellen und Nachweise

ORD-Eintrag
ord-e2d5d251e04e40498c31088368b63d64
Quelldatensatz
uspto-grants-1982_08
Patentnummer
US04346224

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