Water → Benzyl 4-(oxiran-2-yl)piperidine-1-carboxylate

HRID 1971145Notes

Reaction equation

HRID 1971145 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[CH:9]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[CH2:13][CH2:12]1)=[O:10].O>CS(C)=O>[O:10]1[CH2:2][CH:9]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 2776272Benzyl 4-formylpiperidine-1-carboxylate

Product 1

HCID 59305139Benzyl 4-(oxiran-2-yl)piperidine-1-carboxylateYield 73%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Trimethylsulfoxonium iodide (1.65 g, 7.5 mmol) was added in two portions to a solution of NaH (300 mg, 7.5 mmol) in anhydrous DMSO (10 mL) at room temperature. The resulting mixture was stirred for 1 hour, whereupon a solution of phenylmethyl 4-formyl-1-piperidinecarboxylate (1.24 g, 5.0 mmol) in anhydrous DMSO (10 mL) was added. The reaction mixture was stirred at room temperature for 2 hours, then poured into cold water (100 mL), and extracted with Et2O (2×100 mL). The extracts were combined, washed with water, brine, and dried (Na2SO4). The solvent was removed in vacuo to give the title compound (0.95 g, 73%) as a colorless oil. MS (ES) m/e 262 [M+H]+.

Workup

  1. additionwas added
  2. extractionextracted with Et2O (2×100 mL)
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-225aff00df0345c09083dd12caabe794
Source dataset
uspto-grants-2013_04
Patent number
US08431590B2

Reaction notes

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