Methyl chloroformate → Dimethyl 2-(2,6-difluorobenzyl)piperidine-1,4-dicarboxylate

HRID 1963315Notes

Reaction equation

HRID 1963315 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][NH:6]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:18]=[CH:17][CH:16]=[C:15]([F:19])[C:3]=1[CH2:4][CH:5]1[CH2:10][CH:9]([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][N:6]1[C:29]([O:30][CH3:31])=[O:32]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731568Methyl 2-(2,6-difluorobenzyl)piperidine-4-carboxylate

Product 1

HCID 66734964Dimethyl 2-(2,6-difluorobenzyl)piperidine-1,4-dicarboxylateYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(2,6-difluorobenzyl)piperidine-4-carboxylate (5.008 g, 18.60 mmol) was dissolved in DCM (121 mL) and DIPEA (3.89 mL, 22.32 mmol) followed by methyl carbonochloridate (2.050 mL, 26.04 mmol) were added. After 3.5 h at room temperature the solution was washed with 0.1 M HCl and satd NaHCO3. The organic phase was dried and concentrated to yield dimethyl 2-(2,6-difluorobenzyl)piperidine-1,4-dicarboxylate (5.98 g, 98%). MS m/z 328 (M+H)+

Workup

  1. additionwere added
  2. washAfter 3.5 h at room temperature the solution was washed with 0.1 M HCl
  3. customThe organic phase was dried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e2011a64e76a4ee08adf1e03cd6e9d97
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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