Trifluoroacetic acid → HCID 66787314, compound

HRID 2194002Notes

Reaction equation

HRID 2194002 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][CH2:21][O:22][CH3:23])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66788050HCID 66788050, compound

Product 1

HCID 66787314HCID 66787314, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(3-Methoxy-propyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (6 g) was dissolved in methylene chloride (200 ml) under an argon atmosphere, TFA (35.6 ml) was added and the reaction mixture was stirred for 3 hours at RT. The solvent together with most of the TFA was evaporated off, the residue dissolved in methylene chloride (800 ml) and treated with 2M KHCO3 under ice cooling. The layers were separated, the organic layer was washed with water and brine, dried over sodium sulphate and concentrated in vacuo to give 3.63 g of 4-(3-methoxy-propyl)-piperidine-4-carboxylic acid ethyl ester as a light brown oil which was used in next reaction step without further purification.

Workup

  1. customThe solvent together with most of the TFA was evaporated off
  2. dissolutionthe residue dissolved in methylene chloride (800 ml)
  3. additiontreated with 2M KHCO3 under ice cooling
  4. customThe layers were separated
  5. washthe organic layer was washed with water and brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7db82cd296c6464bbaba4db4b24e2c5f
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

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