Methyl chloroformate → Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963268Notes

Reaction equation

HRID 1963268 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]2)=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:31])[O:29][CH3:30]>C(Cl)Cl.C(Cl)(=O)OC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]2[C:28]([O:29][CH3:30])=[O:31])=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731633HCID 66731633, compound

Product 1

HCID 66735290Dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylateYield 95%

Reagents, catalysts & solvents 2

HCID 6586Methyl chloroformateCatalystHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-fluorobenzyl)piperidine-4-carboxylate (4.981 g, 19.82 mmol) was dissolved in DCM (150 mL) and DIPEA (4.14 mL, 23.79 mmol), then methyl carbonochloridate (1.873 mL, 23.79 mmol) was added. The solution was stirred at room temperature for 50 min. More methyl carbonochloridate (a few drops) were added and the reaction continued at room temperature for 1 h. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-(4-fluorobenzyl)piperidine-1,4-dicarboxylate (5.82 g, 95%) as a yellow oil. MS m/z 310 (M+H)+

Workup

  1. waitthe reaction continued at room temperature for 1 h
  2. washThe reaction mixture was washed with 0.1 M HCl
  3. customevaporated

Sources & evidence

ORD record
ord-9e4c0eaf21e74859b736c37e41ad6eb0
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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