m-Chloroperbenzoic acid → HCID 86680143, compound

HRID 1915944Notes

Reaction equation

HRID 1915944 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[CH2:12]=[C:13]1[CH2:19][N:18]([C:20]2[N:21]([CH3:28])[N:22]=[CH:23][C:24]=2[N+:25]([O-:27])=[O:26])[CH2:17][CH2:16][C@H:15]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:14]1>C(Cl)Cl>[CH3:28][N:21]1[C:20]([N:18]2[CH2:19][C:13]3([CH2:12][O:9]3)[CH2:14][C@@H:15]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH2:16][CH2:17]2)=[C:24]([N+:25]([O-:27])=[O:26])[CH:23]=[N:22]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86680141HCID 86680141, compound

Product 1

HCID 86680143HCID 86680143, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

MCPBA (335 mg, 1.49 mmol, 77 mass %) was added to a stirred solution of tert-butyl N-[(4R)-6-methylene-1-(2-methyl-4-nitro-pyrazol-3-yl)azepan-4-yl]carbamate (350 mg, 1.00 mmol) in DCM (12 mL). The mixture was stirred at room temperature overnight. The reaction was quenched with sat NaHCO3 and extracted with DCM 3×. The combined organic layers were concentrated and the residue was purified via silica gel column chromatography (0-100% EA/heptane) to give tert-butyl N-[(5S)-8-(2-methyl-4-nitro-pyrazol-3-yl)-2-oxa-8-azaspiro[2.6]nonan-5-yl]carbamate (316 mg, 86%).

Workup

  1. customThe reaction was quenched with sat NaHCO3
  2. extractionextracted with DCM 3×
  3. concentrationThe combined organic layers were concentrated
  4. customthe residue was purified via silica gel column chromatography (0-100% EA/heptane)

Sources & evidence

ORD record
ord-014fc9f33dd34fffb220d9e8442e0b41
Source dataset
uspto-grants-2013_12
Patent number
US08614206B2

Reaction notes

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