Methyl iodide → HCID 86729355, compound

HRID 521189Notes

Reaction equation

HRID 521189 reaction equation
[CH3:1]I.[H-].[Na+].[C:5]([CH2:7]P(=O)(OCC)OCC)#[N:6].O=[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1>CN(C=O)C>[C:5]([C:7](=[C:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]1)[CH3:1])#[N:6]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 75676Diethyl (cyanomethyl)phosphonateHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 86729355HCID 86729355, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of MeI (1.4 g, 10 mmol) in DMF was added NaH (0.40 g, 10 mmol, 60% in mineral oil), followed by diethyl (cyanomethyl)phosphonate (2.3 g, 10 mmol). The mixture was stirred at ambient temperature. After 30 minutes another batch of NaH (0.40 g, 10 mmol, 60% in mineral oil) was added, followed by tert-butyl 4-oxopiperidine-1-carboxylate (2.0 g, 10 mmol). The resulting mixture was stirred for 30 minutes before the reaction was quenched with water and the mixture was concentrated in vacuo. The crude residue was purified by MPLC on silica gel to afford the title compound. LRMS (ESI) calc'd for C13H21N2O2 [M+H]+237. Found 237.

Workup

  1. stirringThe resulting mixture was stirred for 30 minutes before the reaction
  2. customwas quenched with water
  3. concentrationthe mixture was concentrated in vacuo
  4. customThe crude residue was purified by MPLC on silica gel

Sources & evidence

ORD record
ord-b7273614e8d14973b48ae59d22101cb3
Source dataset
uspto-grants-2016_05
Patent number
US09328099B2

Reaction notes

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