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

HRID 67800Notes

Reaction equation

HRID 67800 reaction equation
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]

Participants

5

Reactant 4

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

Product 1

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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e2d5d251e04e40498c31088368b63d64
Source dataset
uspto-grants-1982_08
Patent number
US04346224

Reaction notes

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