Methyl iodide → HCID 59352893, compound

HRID 1945740Notes

Reaction equation

HRID 1945740 reaction equation
[H-].[Na+].[CH3:3]I.[OH:5][C:6]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)([CH3:8])[CH3:7]>C1COCC1>[CH3:3][O:5][C:6]([CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][CH2:10]1)([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21949386HCID 21949386, compound

Product 1

HCID 59352893HCID 59352893, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a suspension of sodium hydride, 60% dispersion in mineral oil (0.322 g) and methyl iodide (1.00 mL) in 10 mL THF at room temp was carefully added portionwise benzyl 4-(2-hydroxypropan-2-yl)piperidine-1-carboxylate (1.49 g, 0.00537 mol) in 15 mL THF. The reaction was heated at 50° C. for 18 hours and then it was cooled down to 0° C. and carefully quenched by addition of sat NH4Cl solution, then extracted with EtOAc twice. The combined organics were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash chrom to get 1.2 g benzyl 4-(2-methoxypropan-2-yl)piperidine-1-carboxylate as a colorless oil.

Workup

  1. temperatureit was cooled down to 0° C.
  2. customcarefully quenched by addition of sat NH4Cl solution
  3. extractionextracted with EtOAc twice
  4. washThe combined organics were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chrom

Sources & evidence

ORD record
ord-4371b002dfd9440f9db79a469d76a77b
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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