Methyl chloroformate → HCID 66734661, compound

HRID 1963159Notes

Reaction equation

HRID 1963159 reaction equation
Cl.[CH3:2][S:3]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][NH:13]2)=[CH:8][CH:7]=1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33]>C(Cl)Cl>[CH3:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]([CH:12]2[CH2:17][CH:16]([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:14][N:13]2[C:31]([O:32][CH3:33])=[O:34])=[CH:10][CH:11]=1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731560HCID 66731560, compound

Product 1

HCID 66734661HCID 66734661, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl 2-(4-(methylsulfonyl)phenyl)piperidine-4-carboxylate hydrochloride (5.2 g, 15.58 mmol) and DIPEA (6.78 mL, 38.94 mmol) were dissolved in DCM (40 mL) and methyl carbonochloridate (1.472 mL, 18.69 mmol) added. The reaction was stirred at room temperature for 50 min. DCM (160 mL) was added. The organic phase was washed with 0.1 M HCl (2×200 mL), satd NaHCO3 (200 mL), dried with a phase separator and evaporated in vacuo yielding crude dimethyl 2-(4-(methylsulfonyl)phenyl)piperidine-1,4-dicarboxylate (5.95 g, 108%). MS m/z 356 (M+H)+

Workup

  1. washThe organic phase was washed with 0.1 M HCl (2×200 mL), satd NaHCO3 (200 mL)
  2. customdried with a phase separator
  3. customevaporated in vacuo

Sources & evidence

ORD record
ord-f892d43734534672818360ff888483b6
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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