Methyl chloroformate → HCID 66734649, compound

HRID 1963279Notes

Reaction equation

HRID 1963279 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:19]=[CH:18][C:6]([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][NH:9]2)=[CH:5][CH:4]=1.CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33]>ClCCl.CCOCC>[F:21][C:2]([F:1])([F:20])[C:3]1[CH:4]=[CH:5][C:6]([CH2:7][CH:8]2[CH2:13][CH:12]([C:14]([O:16][CH3:17])=[O:15])[CH2:11][CH2:10][N:9]2[C:31]([O:32][CH3:33])=[O:34])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732410HCID 66732410, compound

Product 1

HCID 66734649HCID 66734649, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-(trifluoromethyl)benzyl)piperidine-4-carboxylate (9.5 g, 31.53 mmol) was dissolved in DIPEA (8.24 mL, 47.29 mmol) and dichloromethane (150 mL). Methyl carbonochloridate (3.58 g, 37.50 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 1 h, diluted with ether and washed with 1 M HCl. The organic layer was washed with Na2CO3 (aq), dried MgSO4, filtered through celite and the solvent was evaporated to yield dimethyl 2-(4-(trifluoromethyl)benzyl)piperidine-1,4-dicarboxylate (10.9 g, 96%).

Workup

  1. washwashed with 1 M HCl
  2. washThe organic layer was washed with Na2CO3 (aq), dried MgSO4
  3. filtrationfiltered through celite
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-22e22413304741d59802d00113020fa8
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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