Methyl iodide → HCID 67772452, compound

HRID 1808858Notes

Reaction equation

HRID 1808858 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:25]=[CH:24][C:7]([C:8]([N:10]([C@@H:12]([CH2:21][CH2:22][CH3:23])[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16][CH2:15]2)[CH3:11])=[O:9])=[CH:6][CH:5]=1.[CH3:26]I>C1COCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]([C@@H:12]([CH2:21][CH2:22][CH3:23])[CH2:13][N:14]2[CH2:19][CH2:18][CH:17]([O:20][CH3:26])[CH2:16][CH2:15]2)[CH3:11])=[O:9])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67773171HCID 67773171, compound

Product 1

HCID 67772452HCID 67772452, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

NaH (21.24 mg, 0.89 mmol) was added to a solution of (S)-4-chloro-N-(1-(4-hydroxypiperidin-1-yl)pentan-2-yl)-N-methylbenzamide (Example 44) (200 mg, 0.59 mmol) in dry THF (10 mL) at room temperature under N2. After 5 min was MeI (0.037 mL, 0.59 mmol) added. The reaction was stirred overnight and was then quenched by addition of NH3 saturated H2O (2 mL). The resulting solution was evaporated and the remainder was dissolved in EtOAc and poured on an SCX-2 column (5 g). The column was washed with MeOH and the product was eluted by NH3 saturated MeOH. The crude product was purified by preparative HPLC to yield the title product (106 mg, 51.0%). 1H NMR (600 MHz, DMSO-d6) δ 0.78, 0.91, 1.05-1.51, 1.70-1.84, 1.91-2.03, 2.09-2.13, 2.17-2.23, 2.33-2.39, 2.41-2.54, 2.58-2.64, 2.76, 2.82, 3.12, 3.19-3.22, 3.53-3.59, 4.71-4.79, 7.31-7.35, 7.36-7.40, 7.47-7.53. HRMS (M+H)+: calculated 353.1996. found 353.2006.

Workup

  1. customwas then quenched by addition of NH3 saturated H2O (2 mL)
  2. customThe resulting solution was evaporated
  3. dissolutionthe remainder was dissolved in EtOAc
  4. additionpoured on an SCX-2 column (5 g)
  5. washThe column was washed with MeOH
  6. washthe product was eluted by NH3 saturated MeOH
  7. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-a9e97d5e5b5e4918b9fe43e16cadd523
Source dataset
uspto-grants-2013_01
Patent number
US08361998B2

Reaction notes

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