HCID 86756025, compound → HCID 86756024, compound

HRID 1857492Notes

Reaction equation

HRID 1857492 reaction equation
C(OC([N:11]1[C:20]2[C:15](=[CH:16][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:18][CH:19]=2)[C@H:14]([N:25]([CH2:30][C:31]2[CH:36]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=2)[C:26]([O:28][CH3:29])=[O:27])[CH2:13][C@@H:12]1[CH3:45])=O)C1C=CC=CC=1.[H][H]>[Pd].C(O)C>[CH3:29][O:28][C:26](=[O:27])[N:25]([CH2:30][C:31]1[CH:36]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:34]=[C:33]([C:41]([F:44])([F:43])[F:42])[CH:32]=1)[C@H:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[NH:11][C@@H:12]([CH3:45])[CH2:13]1

Participants

5

Reactant 2

HCID 86756025HCID 86756025, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86756024HCID 86756024, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid benzyl ester. (Example 56) (2.8 g, 4.3 mmol), ethanol (50 mL), and 10% palladium on carbon (280 mg) were combined in a Parr bottle and agitated under 50 psi of hydrogen gas on a Parr shaker for 0.5 h. The mixture was then filtered through a bed of Celite®, eluting with ethyl acetate, and the filtrate concentrated in vacuo. The residue was purified by silica gel chromatography using 5% ethyl acetate/hexanes as eluent to afford 2.0 g of the title product (90%): MS m/z 516 (M+ +2); 1H NMR (CDCl3) δ 1.18 (C2-Me, d, 3H, J=5.8 Hz), 6.50 (C8, d, 1H, J=8.3 Hz), 7.21 (C7, d, 1H, J=8.5).

Workup

  1. filtrationThe mixture was then filtered through a bed of Celite®
  2. washeluting with ethyl acetate
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-51adefbcb201409b95c568549667608d
Source dataset
uspto-grants-2000_11
Patent number
US06147090

Reaction notes

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