Trifluoroacetic acid → 4-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

HRID 2193994Notes

Reaction equation

HRID 2193994 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][O:21][CH3:22])[CH2:11][CH2:10][N:9](C(OC(C)(C)C)=O)[CH2:8][CH2:7]1)=[O:5])[CH3:2].FC(F)(F)C(O)=O.[OH-].[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][O:21][CH3:22])[CH2:7][CH2:8][NH:9][CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 582872614-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 567539694-(2-Methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-(2-Methoxy-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (8 g) was dissolved in methylene chloride (40 ml), trifluoroacetic acid (75.57 g, 50.72 ml) was added under an argon atmosphere at RT and the mixture was stirred for 2 hours until completion of the reaction. The reaction mixture was diluted with dichloromethane (500 ml), and then 3M NaOH (220.9 ml) was slowly added. The layers were separated, the organic layer washed with brine, dried over sodium sulphate and concentrated to give 4-(2-methoxy-ethyl)-piperidine-4-carboxylic acid ethyl ester a brown oil (3.76 g) which was essentially pure according to NMR and used in next reaction step without further purification. MS (ESI): 216.3 (MH+).

Workup

  1. customThe layers were separated
  2. washthe organic layer washed with brine
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-740456c736c64e67a22c0cecf27e3b10
Source dataset
uspto-grants-2012_12
Patent number
US08329904B2

Reaction notes

Loading…