Sodium hydride → N-Cyclobutylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline

HRID 904760Notes

Reaction equation

HRID 904760 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]23[CH2:18][CH2:17][CH2:16][CH:15]=[C:14]2[C:13](=[O:19])[NH:12][C:11](=[O:20])[CH2:10]3)[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH:23]1([CH2:27]CS([O-])(=O)=O)[CH2:26][CH2:25][CH2:24]1>CN(C)C=O>[CH:23]1([CH2:27][N:12]2[C:11](=[O:20])[CH2:10][C:9]3([C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=4)[C:14](=[CH:15][CH2:16][CH2:17][CH2:18]3)[C:13]2=[O:19])[CH2:26][CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 132819714a-(m-Methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinolineHCID 131713239Cyclobutylmethylmesylate

Product 1

HCID 13281976N-Cyclobutylmethyl-4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The procedure in Example 9, Part A was followed in which 4a-(m-methoxyphenyl)-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinoline (10.74 g) in 135 ml of anhydrous dimethylformamide was added to a 55% suspension of sodium hydride in mineral oil (2.15 g) in 90 ml of dimethylformamide at 70° C. Cyclobutylmethylmesylate (9 g) was added and the reaction heated at 80°-90° C. for 6 hours, then at 25° C. for 10 hours. This gave, after chromatography, a crystalline product (6 g), mp 89°-93° C.

Workup

  1. temperaturethe reaction heated at 80°-90° C. for 6 hours

Sources & evidence

ORD record
ord-3905eb58871b4e4fa57e4850a4e3d3a5
Source dataset
uspto-grants-1983_12
Patent number
US04419517

Reaction notes

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