Methyl iodide → HCID 15884733, compound

HRID 379520Notes

Reaction equation

HRID 379520 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[CH2:10][CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:23]I.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH3:23])[CH2:10][CH:9]1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15884732HCID 15884732, compound

Product 1

HCID 15884733HCID 15884733, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(tert-butoxycarbonyl)-2-(2-methoxyphenyl)-4-hydroxypiperidine (910 mg, 2.94 mmol) in DMF (10 mL) at 0° C. was added methyl iodide (0.92 mL, 14.8 mmol) and NaH (236 mg, 5.9 mmol) and the resulting suspension was stirred at room temperature for 2 hours. The reaction mixutre was quenched with H2O at 0° C., EtOAc was added, and the aqueous layer was extracted with EtOAc (×4). The combined organic layers were washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo to provide the title compound as a colorless oil (898 mg). 1H NMR (CDCl3, 400 MHz) δ:3.82 (3H, s, OMe), 3.10 (3H, s, OMe), and 1.22 (9H, s, Bu-t).

Workup

  1. customThe reaction mixutre was quenched with H2O at 0° C.
  2. additionEtOAc was added
  3. extractionthe aqueous layer was extracted with EtOAc (×4)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d94089c62334412984fdbb55a38478d9
Source dataset
uspto-grants-2001_10
Patent number
US06300316B1

Reaction notes

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