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

HRID 2061043Notes

Reaction equation

HRID 2061043 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 673106161-(2-(3-(Benzyloxycarbonylamino)-3-methylbutanoyloxy)ethyl)-1-methylpiperidinium iodideYield 66.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-ee26e2c2ed8b41c7b912640d4d442c61
Source dataset
uspto-grants-2012_10
Patent number
US08278482B2

Reaction notes

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