Reaction #54066

ord-44529c863784495ba0268ab73cd417bc

Reaction equation

COc1ccccc1-c1ccc2c(c1)C(C(C)O)=CC(C)(C)N2C(=O)OC(C)(C)C.COc1ccccc1-c1ccc2c(c1)C(C(C)OCC1CCCCC1)=CC(C)(C)N2

4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

sodium bis(trimethylsilyl)amide

cyclohexylmethyl bromide

→

C/C=C/COC(C)C1=CC(C)(C)Nc2ccc(-c3ccccc3OC)cc21

title compound

Yield 25.6%

4-{1-[((E)-but-2-enyl)oxy]ethyl}-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline

Yield 25.6%

Reactants

—

solution

4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester

sodium bis(trimethylsilyl)amide

cyclohexylmethyl bromide

Reagents

None

Solvents

THF

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

1
Otherto give the alkylated product, which

Procedure

4-(1-Cyclohexylmethoxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-1,2-dihydroquinoline 4-(1-Hydroxyethyl)-6-(2-methoxyphenyl)-2,2-dimethyl-2H-quinoline-1-carboxylic acid tert-butyl ester (70 mg) was treated with 255 μL of 1 M solution of sodium bis(trimethylsilyl)amide in THF and 45 mg of cyclohexylmethyl bromide to give the alkylated product, which was deprotected to yield 8 mg of the title compound as an oil.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858627B2uspto-grants-2005_02