Triethylamine → 7,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid methyl ester

HRID 927573Notes

Reaction equation

HRID 927573 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][C:10]2[N:9]=[C:8](OS(C(F)(F)F)(=O)=O)[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:28]([O:31][CH2:32]C)(=[O:30])C>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:32][O:31][C:28]([C:8]1[CH:7]=[CH:6][C:5]2[CH2:4][CH2:3][C:2]([CH3:20])([CH3:1])[CH2:11][C:10]=2[N:9]=1)=[O:30]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 86674768Trifluoro-methanesulfonic acid 7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-2-yl ester

Product 1

HCID 710873877,7-Dimethyl-5,6,7,8-tetrahydro-quinoline-2-carboxylic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 887MethanolSolvent

Procedure

Trifluoro-methanesulfonic acid 7,7-dimethyl-5,6,7,8-tetrahydro-quinolin-2-yl ester (3.1 g, 10.0 mmol) was dissolved in methanol (45 mL) and ethyl acetate (45 mL). PdCl2(dppf)-CH2Cl2 adduct (311 mg, 381 μmol) and triethylamine (1.52 g, 2.1 mL, 15.0 mmol) were added and the mixture was stirred in an autoclave at 110° C. with a CO pressure of 70 bar for 24 h. The solvents were evaporated to give a red-brown oily residue that was purified by gradient chromatography on silica with ethyl acetate in heptane. The chromatography yielded 1.9 g (86%) of the title compound as white solid; LC-MS (UV peak area/EIC) 100%, 220.1335 (M+H)+.

Workup

  1. customThe solvents were evaporated
  2. customto give a red-brown oily residue that
  3. customwas purified by gradient chromatography on silica with ethyl acetate in heptane

Sources & evidence

ORD record
ord-409610c9628f453a86645b72bf44f251
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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