Pyridine → cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl ester

HRID 382343Notes

Reaction equation

HRID 382343 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][CH2:16][C:13]=3[CH:14]=2)[C@H:9]([NH:19][CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=2)[CH2:8][C@@H:7]1[CH3:35])=[O:5])[CH3:2].N1C=CC=CC=1.Cl[C:43]([O:45][CH3:46])=[O:44]>ClCCl.C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]3[CH2:18][CH2:17][CH2:16][C:13]=3[CH:14]=2)[C@H:9]([N:19]([CH2:20][C:21]2[CH:22]=[C:23]([C:31]([F:34])([F:32])[F:33])[CH:24]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:26]=2)[C:43]([O:45][CH3:46])=[O:44])[CH2:8][C@@H:7]1[CH3:35])=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 1049PyridineHCID 6586Methyl chloroformateHCID 86755976HCID 86755976, compound

Product 1

HCID 60044672cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl esterYield 70.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

cis-4-(3,5-Bis-trifluoromethyl-benzylamino)-2-methyl-2,3,4,6,7,8-hexahydro-cyclopenta[g]quinoline-1-carboxylic acid ethyl ester (Example 4) (1.30 g, 2.55 mmol) was dissolved in anhydrous dichloromethane (100 mL), and pyridine (2.05 mL, 25.5 mmol) was added. The mixture was cooled to 0° C., and methyl chloroformate (1.97 mL, 25.5 mmol) was slowly added over 20 min. The reaction was stirred at 0° C. for 1 h, then at room temperature for 18 h. The reaction mixture was then diluted with chloroform, and washed twice with 1N HCl. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel chromatography using 10% ethyl acetate/hexanes as eluent afforded the title compound (1.00 g). MS m/z 558 (M+); 1H NMR (CDCl3) δ1.1(d, 3H), 2.9 (m, 4H), 3.8 (s, 3H), 6.8 (s, 1H), 7.3 (s, 1H).

Workup

  1. waitat room temperature for 18 h
  2. washwashed twice with 1N HCl
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-a3d44aad05e44fd6b3c98304aa44e196
Source dataset
uspto-grants-2001_10
Patent number
US06310075B1

Reaction notes

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