Methyl iodide → 1-(2-(3-(Benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodide

HRID 2061043

Reaktionsgleichung

Reaktionsgleichung von HRID 2061043
[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]([O:16][CH2:17][CH2:18][N:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][I:28]>ClCCl>[I-:28].[CH2:1]([O:8][C:9]([NH:11][C:12]([CH3:26])([CH3:25])[CH2:13][C:14]([O:16][CH2:17][CH2:18][N+:19]1([CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 601344582-(Piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate

Produkt 1

HCID 673106161-(2-(3-(Benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodideAusbeute 66,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A batch of 2-(piperidin-1-yl)ethyl 3-(benzyloxycarbonylamino)-3-methylbutanoate (9.45 g, 26.1 mmol) was dissolved in a solution of dichloromethane (40 ml) and methyl iodide (16.3 ml, 262 mmole). The mixture was stirred at room temperature for 18 hours. The reaction mixture was concentrated in vacuo, and the crude material was purified by pre-HPLC to give 8.74 g (66%) of 1-(2-(3-(benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodide. 1H NMR (CD3OD) δ 7.39-7.27 (m, 5 H), 5.05 (s, 2 H), 4.52-4.47 (m, 2 H), 3.70-3.64 (m, 2 H), 3.44-3.37 (m, 4 H), 3.09 (s, 3 H), 2.84 (s, 2 H), 1.92-1.86 (m, 4 H), 1.73-1.59 (m, 2 H), 1.39 (s, 6 H). MS (ESI+) calculated for C21H33N2O4+: 377.24, Found: 377.2 (M+).

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude material was purified by pre-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-ee26e2c2ed8b41c7b912640d4d442c61
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278482B2

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