Trifluoroacetic acid → 2,2-Dimethyl-3-(piperidine-4-yl)-propionic acid methyl ester

HRID 1691858Notes

Reaction equation

HRID 1691858 reaction equation
[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:20])([CH3:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:21])[C:4]([CH3:19])([CH3:20])[CH2:5][CH:6]1[CH2:11][CH2:10][NH:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 592610682,2-dimethyl-3-(N-Boc-piperidine-4-yl)-propionic acid methyl ester

Product 1

HCID 592610232,2-Dimethyl-3-(piperidine-4-yl)-propionic acid methyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-dimethyl-3-(N-Boc-piperidine-4-yl)-propionic acid methyl ester (598 mg) from above was dissolved in methylene chloride (2 mL) and trifluoroacetic acid (1 mL) was added. The mixture was stirred at room temperature for 1 hr and the solvents were evaporated. The mixture was partitioned between ether and sodium hydroxide solution (1N). The organic layer was washed with brine and dried. Evaporation of solvents gave 2,2-dimethyl-3-(piperidine-4-yl)-propionic acid methyl ester (370 mg) as an oil.

Workup

  1. customthe solvents were evaporated
  2. customThe mixture was partitioned between ether and sodium hydroxide solution (1N)
  3. washThe organic layer was washed with brine
  4. customdried
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-9625ae5bfbe348d7a1d352b39fdd3777
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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