Methyl chloroformate → HCID 59536558, compound

HRID 1963248Notes

Reaction equation

HRID 1963248 reaction equation
[F:1][CH:2]([F:13])[CH:3]1[CH2:8][CH:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][NH:4]1.CCN(C(C)C)C(C)C.[C:23](Cl)(=[O:26])[O:24][CH3:25].[NH4+].[Cl-]>ClCCl>[F:13][CH:2]([F:1])[CH:3]1[CH2:8][CH:7]([C:9]([O:11][CH3:12])=[O:10])[CH2:6][CH2:5][N:4]1[C:23]([O:24][CH3:25])=[O:26]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 59536564HCID 59536564, compound

Product 1

HCID 59536558HCID 59536558, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(difluoromethyl)piperidine-4-carboxylate (1.85 g, 9.58 mmol) was dissolved in dichloromethane (50 mL), DIPEA (2.335 mL, 13.41 mmol) and methyl carbonochloridate (0.905 mL, 11.49 mmol) were added and the mixture was stirred at room temperature for 3 h. 0.1 M NH4Cl was added and the aqueous layer was extracted with DCM. The combined organic layers were filtered through a phase separator and evaporated. Crude dimethyl 2-(difluoromethyl)piperidine-1,4-dicarboxylate (2.35 g, 98%) was isolated.

Workup

  1. extractionthe aqueous layer was extracted with DCM
  2. filtrationThe combined organic layers were filtered through a phase separator
  3. customevaporated

Sources & evidence

ORD record
ord-a1f562e602874424b19f2288d220f089
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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