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

HRID 1963244Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1963244
[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

Komponenten

6

Edukt 4

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

Produkt 1

HCID 59536557Dimethyl 2-(cyclohexyloxymethyl)piperidine-1,4-dicarboxylateAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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)+

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bec1b2006e0441d4acdcc1aa8ba8d3af
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08415378B2

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