Dichloromethane → 4-(4-Hydroxy-phenyl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

HRID 2428169Notes

Reaction equation

HRID 2428169 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH3:19][O:20][C:21]([C:23]1[CH2:24][N:25]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:26][CH2:27][C:28]=1[C:29]1[CH:34]=[CH:33][C:32]([O:35][Si](C(C)(C)C)(C)C)=[CH:31][CH:30]=1)=[O:22].C(Cl)Cl>C1COCC1>[CH3:19][O:20][C:21]([C:23]1[CH2:24][N:25]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:26][CH2:27][C:28]=1[C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1)=[O:22]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 2724141Tetrabutylammonium FluorideHCID 671485964-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl Ester

Product 1

HCID 671482474-(4-Hydroxy-phenyl)-5,6-dihydro-2H-pyridine-1,3-dicarboxylic Acid 1-tert-butyl Ester 3-methyl EsterYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

TBAF (9.50 g, 30 mmol) was added to a sol. of compound B1 (13.4 g, 30 mmol) in THF (100 mL) at 0° C. The mixture was stirred at 0° C. for 1 h. CH2Cl2 was added, and the mixture was washed with aq. sat. NH4Cl, water, and brine. The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Drying the residue under high vacuum yielded the crude title compound (10.0 g, quantitative yield) that was used further without purification. LC-MS: tR=0.92 min; ES+: 334.23.

Workup

  1. washthe mixture was washed with aq. sat. NH4Cl, water, and brine
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customDrying the residue under high vacuum

Sources & evidence

ORD record
ord-e85fe98e795040f4998b7deebb97cec8
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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