Methyl chloroformate → HCID 66732437, compound

HRID 1963229Notes

Reaction equation

HRID 1963229 reaction equation
[C:1]1([CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCN(C(C)C)C(C)C.[C:26](Cl)(=[O:29])[O:27][CH3:28]>C(Cl)Cl>[C:1]1([CH:7]2[CH2:12][CH:11]([C:13]([O:15][CH3:16])=[O:14])[CH2:10][CH2:9][N:8]2[C:26]([O:27][CH3:28])=[O:29])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6586Methyl chloroformate2×HCID 81531Diisopropylethylamine2×HCID 22831677HCID 22831677, compound

Product 1

HCID 66732437HCID 66732437, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-phenylpiperidine-4-carboxylate (4.33 g, 19.75 mmol) was dissolved in DCM (150 mL) and DIPEA (3.78 mL, 21.72 mmol), then methyl carbonochloridate (1.710 mL, 21.72 mmol) was added. The solution was stirred at room temperature for 1 h 45 min. More DIPEA (1.720 mL, 9.87 mmol) and methyl carbonochloridate (0.777 mL, 9.87 mmol) were added and the reaction continued at room temperature for another 30 min. The reaction mixture was washed with 0.1 M HCl and satd NaHCO3. The organic phase was passed through a phase separator and evaporated to yield dimethyl 2-phenylpiperidine-1,4-dicarboxylate (5.88 g, quant.) as a yellow oil. MS m/z 278 (M+H)+

Workup

  1. waitthe reaction continued at room temperature for another 30 min
  2. washThe reaction mixture was washed with 0.1 M HCl
  3. customevaporated

Sources & evidence

ORD record
ord-698cdc1ae1cc4399bb40303aeeb34d88
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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