Methyl iodide → HCID 22884165, compound

HRID 1598466Notes

Reaction equation

HRID 1598466 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@@H:10]([CH2:21][CH2:22][CH2:23][OH:24])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:27]I>CN(C=O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[C@@H:10]([CH2:21][CH2:22][CH2:23][O:24][CH3:27])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22884164HCID 22884164, compound

Product 1

HCID 22884165HCID 22884165, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the procedure described in Example 7, Step C, except using 4-benzyl-1-tert-butoxycarbonyl-2(S)-(3-hydroxy-1-propyl)piperazine (1.02 g, 3.05 mmol), sodium hydride (0.183 g, 60% dispersion in oil, 4.58 mmol), and methyl iodide (0.247 mL, 3.97 mmol) in DMF (6 mL). The crude product was chromatographed on silica gel with 30% ethyl acetate in hexane to obtain the title compound as a clear oil (0.870 g). NMR (CDCl3, 300 MHz) δ 7.3 (5H, m), 4.05 (1H, m), 3.85 (1H, m), 3.46 (2H, AB q, J=12 Hz, D n=42 Hz), 3.39 (1H, m), 3.22 (3H, s), 3.04 (1H, t, J=13 Hz), 2.74 (1H, d, J=12 Hz), 2.66 (1H, d, J=12 Hz), 1.45-2.12 (7H, m), 1.44 (9H, s).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-282149a88cb04df0b469f932f2788c08
Source dataset
uspto-grants-1998_04
Patent number
US05736539

Reaction notes

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