Cyclohexene → HCID 69831133, compound

HRID 1937458Notes

Reaction equation

HRID 1937458 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([NH:21]C(OCC3C=CC=CC=3)=O)[CH2:10][C@H:11]([CH3:20])[N:12]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=1[O:32][CH3:33])=[O:4].C1CCCCC=1>[Pd].C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([NH2:21])[CH2:10][C@H:11]([CH3:20])[N:12]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=1[O:32][CH3:33])=[O:4]

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 69831999HCID 69831999, compound

Product 1

HCID 69831133HCID 69831133, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

cis-4-Benzyloxycarbonylamino-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-ethyl ester 7-methyl ester (322 mg, 0.71 mmol), 10% palladium on carbon (32 mg) and cyclohexene (9 ml) in 16 ml ethanol was heated to 80° C. for 1.25 h. The reaction mixture was cooled to room temperature, filtered through Celite®, and concentrated in vacuo. Purification by silica gel chromatography using 1% isopropanol-dichloromethane afforded the title product (208 mg, 91%). 1H NMR (DMSO-d6) δ 1.02 (d, 3H), 6.68 (s, 1H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated in vacuo
  3. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-ca1309f4703a4845b92a7c93c4feb016
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

Loading…