Methyl chloroformate → HCID 66732522, compound

HRID 1963232Notes

Reaction equation

HRID 1963232 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].Cl.[CH:7]1([CH:13]2[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][NH:14]2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH:7]1([CH:13]2[CH2:18][CH:17]([C:19]([O:21][CH3:22])=[O:20])[CH2:16][CH2:15][N:14]2[C:2]([O:4][CH3:5])=[O:3])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformate2×HCID 81531Diisopropylethylamine2×HCID 66732187HCID 66732187, compound

Product 1

HCID 66732522HCID 66732522, compoundYield 129.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (1.344 mL, 17.36 mmol) in DCM (50 mL) was added to a solution of methyl 2-cyclohexylpiperidine-4-carboxylate hydrochloride (3.50 g, 13.35 mmol) and DIPEA (1.88 mL, 10.76 mmol) in DCM (100 mL). The reaction solution was stirred for 3 h. 1.88 mL DIPEA and 1.345 mL methyl chloroformate was added and the reaction continued overnight (16 h). The organic phase was washed with satd NaHCO3. The phases were separated and the organic phase dried using a phase separator to give crude dimethyl 2-cyclohexylpiperidine-1,4-dicarboxylate (4.90 g). MS m/z 284 (M+H)+

Workup

  1. customthe reaction continued overnight (16 h)
  2. washThe organic phase was washed with satd NaHCO3
  3. customThe phases were separated
  4. customthe organic phase dried

Sources & evidence

ORD record
ord-63454958bfad4be6ab6c68c5d5626ae6
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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