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

HRID 1577980
Notes
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Reaction equation

HRID 1577980 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 8028
Tetrahydrofuran
Solvent

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-16b243041a5d4c3798f26df96b38954f
Source dataset
uspto-grants-1981_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04289882

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes