Methyl chloroformate → HCID 66734830, compound

HRID 1963255Notes

Reaction equation

HRID 1963255 reaction equation
Cl.[F:2][C:3]1([F:20])[CH2:8][CH2:7][CH:6]([CH2:9][CH:10]2[CH2:15][CH:14]([C:16]([O:18][CH3:19])=[O:17])[CH2:13][CH2:12][NH:11]2)[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[C:30](Cl)(=[O:33])[O:31][CH3:32]>C(Cl)Cl>[F:20][C:3]1([F:2])[CH2:4][CH2:5][CH:6]([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:30]([O:31][CH3:32])=[O:33])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 81531DiisopropylethylamineHCID 66731813HCID 66731813, compound

Product 1

HCID 66734830HCID 66734830, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-((4,4-difluorocyclohexyl)methyl)piperidine-4-carboxylate hydrochloride (5.1 g, 16.36 mmol) was dissolved in DCM (150 mL), then DIPEA (7.14 mL, 40.89 mmol) was added. Methyl carbonochloridate (1.803 mL, 22.90 mmol) was added dropwise to the solution. The mixture was stirred at room temperature for 2 h. The mixture was washed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL), then dried through a phase separator and evaporated yielding crude dimethyl 2-((4,4-difluorocyclohexyl)methyl)piperidine-1,4-dicarboxylate (5.7 g, 105%)

Workup

  1. washThe mixture was washed with 0.1 M HCl (100 mL) and satd NaHCO3 (100 mL)
  2. customdried through a phase separator
  3. customevaporated

Sources & evidence

ORD record
ord-660101d170934172bc4fe11c70e7fc97
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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