Methyl chloroformate → Dimethyl 2-(2,4,5-trifluorophenyl)piperidine-1,4-dicarboxylate

HRID 1963202Notes

Reaction equation

HRID 1963202 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]1.CCN(C(C)C)C(C)C.[C:29](Cl)(=[O:32])[O:30][CH3:31]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[CH:10]1[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]1[C:29]([O:30][CH3:31])=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731764Methyl 2-(2,4,5-trifluorophenyl)piperidine-4-carboxylate

Product 1

HCID 68502002Dimethyl 2-(2,4,5-trifluorophenyl)piperidine-1,4-dicarboxylateYield 109.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(2,4,5-trifluorophenyl)piperidine-4-carboxylate (2.232 g, 8.17 mmol) was dissolved in DCM (50 mL) and DIPEA (1.707 mL, 9.80 mmol), then methyl carbonochloridate (0.965 mL, 12.25 mmol) was added. The solution was stirred at room temperature for 1 h. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3, passed through a phase separator and evaporated to yield crude dimethyl 2-(2,4,5-trifluorophenyl)piperidine-1,4-dicarboxylate (2.971 g, quant.) as a brown oil. MS m/z 332 (M+H)+

Workup

  1. washThe reaction mixture was washed with 0.1 M HCl
  2. customevaporated

Sources & evidence

ORD record
ord-ed73763866364b849fd6ac424b4afea4
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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