Methyl iodide → HCID 89682538, compound

HRID 2278157Notes

Reaction equation

HRID 2278157 reaction equation
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([C:27]3[CH:35]=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)([OH:26])[CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)=[CH:11][C:6]=2[O:5][CH2:4]1.I[CH3:37]>C1COCC1>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([C:12]([C:27]3[CH:35]=[CH:34][C:30]4[O:31][CH2:32][O:33][C:29]=4[CH:28]=3)([O:26][CH3:37])[CH:13]3[CH2:14][CH2:15][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:17][CH2:18]3)=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 89677540HCID 89677540, compound

Product 1

HCID 89682538HCID 89682538, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of NaH (88 mg, 2.2 mmol, 60% in mineral oil) in dry THF (5.0 mL) was added tert-butyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(hydroxy)methyl)piperidine-1-carboxylate (100 mg, 0.22 mmol). After 30 min, iodomethane (468 mg, 143 mmol) was added and the reaction mixture was stirred for an additional 2 h. The reaction was quenched by the addition of a saturated solution of NH4Cl (30 mL) and extracted with EtOAc (3×). The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by SiO2 flash chromatography (20% EtOAc/hexanes) to give tert-butyl 4-(bis(benzo[d][1,3]dioxol-5-yl)(methoxy)-methyl)piperidine-1-carboxylate as a clear viscous oil (94 mg, 91%): 1H NMR 600 MHz (CDCl3) δ 6.79-6.74 (m, 6H), 5.96-5.95 (m, 4H), 4.08 (bs, 2H), 2.86 (s, 3H), 2.76-2.65 (m, 2H), 2.48-2.43 (m, 1H), 1.76 (d, J=13.2 Hz, 3H), 1.38 (s, 9H), 0.94-0.81 (m, 2H).

Workup

  1. customThe reaction was quenched by the addition of a saturated solution of NH4Cl (30 mL)
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by SiO2 flash chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-198bd6a0f25d4eef9ea1713c9437ce70
Source dataset
uspto-grants-2015_09
Patent number
US09133148B2

Reaction notes

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