Methyl chloroformate → HCID 66734904, compound

HRID 1963198Notes

Reaction equation

HRID 1963198 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:11]2[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][NH:12]2)[CH:6]=[C:7]([F:10])[C:8]=1[F:9].CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:33])[O:31][CH3:32]>C(Cl)Cl>[F:10][C:7]1[CH:6]=[C:5]([CH:11]2[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][N:12]2[C:30]([O:31][CH3:32])=[O:33])[CH:4]=[C:3]([F:2])[C:8]=1[F:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731526HCID 66731526, compound

Product 1

HCID 66734904HCID 66734904, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(3,4,5-trifluorophenyl)piperidine-4-carboxylate hydrochloride (2.75 g, 8.88 mmol) was dissolved into DCM (50 mL), then DIPEA (3.88 mL, 22.20 mmol) was added. Methyl carbonochloridate (0.979 mL, 12.43 mmol) was added dropwise to the solution. The mixture was stirred at room temperature for 4 h. The mixture was washed with HCl (0.1 M, 100 mL) and satd NaHCO3 (100 mL), then dried through a phase-separator and evaporated yielding dimethyl 2-(3,4,5-trifluorophenyl)piperidine-1,4-dicarboxylate (2.77 g, 94%) as an orange oil.

Workup

  1. washThe mixture was washed with HCl (0.1 M, 100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase-separator
  3. customevaporated

Sources & evidence

ORD record
ord-504fc5ee27354331bfe4fa0d083185f8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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