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

HRID 1903359Notes

Reaction equation

HRID 1903359 reaction equation
C1CO[C:3]2([CH2:12][CH2:11][C@H:10]3[C@:5]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=4)([CH2:6][CH2:7][N:8]([CH3:14])[C:9]3=[O:13])[CH2:4]2)[O:2]1.CCOCC.[Na+].[Cl-].C(OCC1C(=O)N(C)CCC=1C1C=CC=C(OC)C=1)=O>C1COCC1>[O:13]=[C:9]1[C@@H:10]2[C@@:5]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)([CH2:4][C:3](=[O:2])[CH2:12][CH2:11]2)[CH2:6][CH2:7][N:8]1[CH3:14]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 5234Sodium ChlorideHCID 129475523-Formyloxymethyl-4-(3'-methoxyphenyl)-1-methyl-5,6-dihydro-2-pyridoneHCID 86736843HCID 86736843, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ketal cis-34 (Example 16) (20 mg, 0.06 mmol) was dissolved in 1:1 THF/1 N H2SO4 (2mL) 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 δ7.30 (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-1c51c471c1e1448f91bf97f78238c3f7
Source dataset
uspto-grants-1984_03
Patent number
US04435572

Reaction notes

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