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

HRID 1963276Notes

Reaction equation

HRID 1963276 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][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.Cl[C:29]([O:31][CH3:32])=[O:30]>C(Cl)Cl>[F:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][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:31][CH3:32])=[O:30]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732347Methyl 2-(2-fluorobenzyl)piperidine-4-carboxylate

Product 1

HCID 66734736Dimethyl 2-(2-fluorobenzyl)piperidine-1,4-dicarboxylateYield 112%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(2-fluorobenzyl)piperidine-4-carboxylate (4.49 g, 17.85 mmol) and DIPEA (9.35 mL, 53.55 mmol) in DCM (100 mL) was added methyl chloroformate (1.798 mL, 23.21 mmol) in DCM (50 mL). The reaction mixture was stirred for 1.5 h. The organic phase was washed with satd NaHCO3. The phases were separated and the organic phase dried using a phase separator to yield crude dimethyl 2-(2-fluorobenzyl)piperidine-1,4-dicarboxylate (6.16 g, 112%). MS m/z 310 (M+H)+

Workup

  1. washThe organic phase was washed with satd NaHCO3
  2. customThe phases were separated
  3. customthe organic phase dried

Sources & evidence

ORD record
ord-5a817a8553af454ca944060411037923
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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