Methyl iodide → tert-Butyl 3-(2-fluorobenzyl)-3-(methoxymethyl)piperidine-1-carboxylate

HRID 530884Notes

Reaction equation

HRID 530884 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][C:7]1([CH2:20][OH:21])[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:8]1.I[CH3:27]>C1COCC1>[F:3][C:4]1[CH:25]=[CH:24][CH:23]=[CH:22][C:5]=1[CH2:6][C:7]1([CH2:20][O:21][CH3:27])[CH2:12][CH2:11][CH2:10][N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:17])[CH3:18])=[O:14])[CH2:8]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67983173HCID 67983173, compound

Product 1

HCID 67982981tert-Butyl 3-(2-fluorobenzyl)-3-(methoxymethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (80 mg, 60% in mineral oil, 1.99 mmol) was added to a solution of tert-butyl 3-(2-fluorobenzyl)-3-(hydroxymethyl)piperidine-1-carboxylate (0.43 g, 1.33 mmol) in THF (5 ml) and the reaction mixture was stirred at room temperature for 20 mins. Iodomethane (0.125 ml, 1.99 mmoL) was added to the flask, and the reaction was allowed to stir at room temperature for 16 hrs. The reaction was quenched with water (5 ml) and was extracted using ethyl acetate (20 ml) three times. The ethyl acetate layers were combined, dried over sodium sulfate, filtered, and concentrated. The crude mixture was purified using flash chromatography (0-60% ethyl acetate in hexane) to give the titled compound (0.415 g).

Workup

  1. stirringto stir at room temperature for 16 hrs
  2. customThe reaction was quenched with water (5 ml)
  3. extractionwas extracted
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude mixture was purified

Sources & evidence

ORD record
ord-b74ab21ee26f4766913d55ab443c9df0
Source dataset
uspto-grants-2016_05
Patent number
US09351965B2

Reaction notes

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