Methyl chloroformate → Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylate

HRID 1963244Notes

Reaction equation

HRID 1963244 reaction equation
[CH:1]1([O:7][CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][NH:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CCN(C(C)C)C(C)C.[C:28](Cl)(=[O:31])[O:29][CH3:30].[NH4+].[Cl-]>ClCCl>[CH:1]1([O:7][CH2:8][CH:9]2[CH2:14][CH:13]([C:15]([O:17][CH3:18])=[O:16])[CH2:12][CH2:11][N:10]2[C:28]([O:29][CH3:30])=[O:31])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 59536562Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate

Product 1

HCID 59536557Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylateYield 97.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 2-(cyclohexyloxymethyl)piperidine-4-carboxylate (2.13 g, 8.34 mmol) was dissolved in dichloromethane (50 mL). DIPEA (2.034 mL, 11.68 mmol) and methyl carbonochloridate (0.788 mL, 10.01 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. Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylate (2.54 g, 97%) was isolated. MS m/z 314 (M+H)+

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-bec1b2006e0441d4acdcc1aa8ba8d3af
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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