Sodium hydride → Benzyl 4-(2-phenyloxiran-2-yl)piperidine-1-carboxylate

HRID 509202Notes

Reaction equation

HRID 509202 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[C:9]([CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1>[C:10]1([C:9]2([CH:17]3[CH2:18][CH2:19][N:20]([C:23]([O:25][CH2:26][C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)=[O:24])[CH2:21][CH2:22]3)[CH2:2][O:16]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 57779495Benzyl 4-benzoylpiperidine-1-carboxylate

Product 1

HCID 57779569Benzyl 4-(2-phenyloxiran-2-yl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
55 °C

Procedure

A mixture of trimethylsulfoxonium iodide (2.402 g, 10.91 mmol) and sodium hydride (0.436 g, 10.91 mmol) in THF (20 mL) was heated at 55° C. for 3 h then a solution of compound 87 (2.82 g, 8.73 mmol) in THF (10 mL) was added. The reaction mixture was stirred for 36 h, quenched with water, extracted with ether and the combined organics were washed with water, brine, dried over Na2SO4, filtered and concentrated to afford compound 88 used as a crude in the next step.

Workup

  1. customquenched with water
  2. extractionextracted with ether
  3. washthe combined organics were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-47a0692d80a84ad6abc82a1fbdd45245
Source dataset
uspto-grants-2015_08
Patent number
US09096565B2

Reaction notes

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