cis-4-benzyloxycarbonylamino-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester → cis-4-Amino-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

HRID 369914Notes

Reaction equation

HRID 369914 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:13][CH:14]=2)[C@H:9]([NH:20]C(OCC2C=CC=CC=2)=O)[CH2:8][C@@H:7]1[CH2:31][CH3:32])=[O:5])[CH3:2]>C1CCCCC=1.C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([F:17])([F:18])[F:19])=[CH:13][CH:14]=2)[C@H:9]([NH2:20])[CH2:8][C@@H:7]1[CH2:31][CH3:32])=[O:5])[CH3:2]

Participants

5

Reactant 1

HCID 69578494cis-4-benzyloxycarbonylamino-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester

Product 1

HCID 69580533cis-4-Amino-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl esterYield 69.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8079CyclohexeneSolvent

Procedure

A solution of cis-4-benzyloxycarbonylamino-2-ethyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 3C) (18.0 g, 40 mmol) in 150 mL each of cyclohexene and ethanol was treated with 10% palladium on carbon (10.0 g, 50% water by weight). After heating at reflux for 1 h, the cooled mixture was filtered through Celite® and concentrated in vacuo to afford the crude product, which was purified by silica gel chromatography using 25-50% ethyl acetate/hexanes as eluent to afford 8.8 g of the title product. 1H NMR (CDCl3) δ 0.83 (t, 3H), 1.25 (m, 4H), 1.45 (m, 1H), 1.6 (m, 1H), 2.49 (m, 1H), 3.81 (m, 1H), 4.2 (m, 2H), 4.4 (m, 1H), 7.47 (m, 2H), 7.69 (s, 1H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 1 h
  3. filtrationthe cooled mixture was filtered through Celite®
  4. concentrationconcentrated in vacuo
  5. customto afford the crude product, which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-fbd3df1fc27947679607bdf3d2d0b2d3
Source dataset
uspto-grants-2000_10
Patent number
US06140343

Reaction notes

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