Hydrochloric Acid → 6-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-methyl ester

HRID 1715451Notes

Reaction equation

HRID 1715451 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH2:6][N:7]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:8][CH2:9][C:10]=1[C:11]1[CH:12]=[N:13][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]2[C:26]([Cl:27])=[CH:25][C:24]([CH3:28])=[CH:23][C:22]=2[Cl:29])=[CH:15][CH:16]=1)=[O:4].Cl>CO>[CH3:1][O:2][C:3]([CH:5]1[CH:10]([C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][CH2:19][O:20][C:21]3[C:22]([Cl:29])=[CH:23][C:24]([CH3:28])=[CH:25][C:26]=3[Cl:27])=[CH:15][CH:16]=2)[CH2:9][CH2:8][N:7]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 671490666-[2-(2,6-Dichloro-4-methyl-phenoxy)-ethoxy]-5',6'-dihydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-methyl ester

Product 1

HCID 671488236-[2-(2,6-dichloro-4-methyl-phenoxy)-ethoxy]-3',4',5',6'-tetrahydro-2'H-[3,4']bipyridinyl-1',3'-dicarboxylic acid 1'-tert-butyl ester 3'-methyl esterYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound A2 (7.00 g, 13.0 mmol) was dissolved in MeOH (130 mL). Mg (500 mg, 20.6 mmol) was added slowly. The mixture was stirred for 1 h, and Mg (608 mg, 25.0 mmol) was added again. The mixture was stirred 3 h. Aq. 1M HCl was added slowly, and the mixture was stirred 1 h at rt. The solvents were evaporated under reduced pressure, and the mixture was extracted with EtOAc. The org. extracts were dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying under high vacuum yielded the raw title compound (4.92 g, 70%). LC-MS: tR=1.16 min, ES+=539.43.

Workup

  1. stirringThe mixture was stirred 3 h
  2. stirringthe mixture was stirred 1 h at rt
  3. customThe solvents were evaporated under reduced pressure
  4. extractionthe mixture was extracted with EtOAc
  5. dry with materialextracts were dried over MgSO4
  6. filtrationfiltered
  7. customthe solvents were removed under reduced pressure
  8. customDrying under high vacuum

Sources & evidence

ORD record
ord-d8c78bbf0bab4680886322c11d55436f
Source dataset
uspto-grants-2010_09
Patent number
US07799805B2

Reaction notes

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