Methyl chloroformate → HCID 66734526, compound

HRID 1963303Notes

Reaction equation

HRID 1963303 reaction equation
[CH3:1][S:2]([C:5]1[CH:21]=[CH:20][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CCN(C(C)C)C(C)C.[C:31](Cl)(=[O:34])[O:32][CH3:33]>ClCCl>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][N:11]2[C:31]([O:32][CH3:33])=[O:34])=[CH:20][CH:21]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732452HCID 66732452, compound

Product 1

HCID 66734526HCID 66734526, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(4-(methylsulfonyl)benzyl)piperidine-4-carboxylate (5.88 g, 18.88 mmol) was dissolved in DIPEA (4.93 mL, 28.32 mmol) and dichloromethane (150 mL). Methyl carbonochloridate (2.141 g, 22.66 mmol) was added dropwise and the reaction mixture stirred at room temperature overnight. The solvent was evaporated and the residue partitioned between 1 M KHSO4 and diethyl ether. The organic layer was dried over Na2SO4, filtered through celite and evaporated to yield dimethyl 2-(4-(methylsulfonyl)benzyl)piperidine-1,4-dicarboxylate (5.5 g, 79%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between 1 M KHSO4 and diethyl ether
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered through celite
  5. customevaporated

Sources & evidence

ORD record
ord-03fb2ee4f3d54112bb1ae307a2586a7e
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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