Methyl chloroformate → HCID 66734864, compound

HRID 1963290Notes

Reaction equation

HRID 1963290 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[F:6][C:7]([F:26])([F:25])[C:8]1[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=1[CH2:10][CH:11]1[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][NH:12]1.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:26][C:7]([F:25])([F:6])[C:8]1[CH:24]=[CH:23][CH:22]=[CH:21][C:9]=1[CH2:10][CH:11]1[CH2:16][CH:15]([C:17]([O:19][CH3:20])=[O:18])[CH2:14][CH2:13][N:12]1[C:2]([O:4][CH3:5])=[O:3]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66732323HCID 66732323, compound

Product 1

HCID 66734864HCID 66734864, compoundYield 109%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methyl chloroformate (1.399 mL, 18.07 mmol) in DCM (40 mL) was added to a solution of methyl 2-(2-(trifluoromethyl)benzyl)piperidine-4-carboxylate (4.19 g, 13.9 mmol) and DIPEA (7.28 mL, 41.69 mmol) in DCM (60 mL). The reaction mixture was stirred for 1.5 h at room temperature, then washed with satd NaHCO3. The phases were separated and the organic phase dried using a phase separator to give crude dimethyl 2-(2-(trifluoromethyl)-benzyl)piperidine-1,4-dicarboxylate (5.42 g, 109%). MS m/z 360 (M+H)+

Workup

  1. washwashed with satd NaHCO3
  2. customThe phases were separated
  3. customthe organic phase dried

Sources & evidence

ORD record
ord-54bc9a8d34c348d892bc7b56f95dddac
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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