m-Chloroperbenzoic acid → HCID 85405172, compound

HRID 1500896Notes

Reaction equation

HRID 1500896 reaction equation
[CH:1]1([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH:4]=[CH:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:25])C=1>C(Cl)Cl>[CH:3]12[O:25][CH:4]1[CH2:5][CH:1]([NH:6][C:7](=[O:16])[O:8][CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:2]2

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10751243Benzyl cyclopent-3-en-1-ylcarbamate

Product 1

HCID 85405172HCID 85405172, compoundYield 152%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzyl cyclopent-3-en-1-ylcarbamate (920 mg, 4.23 mmol) in DCM (20 mL), was added m-CPBA (2.0 g, 7.6 mmol) in portions at 0° C. The mixture was warmed up to RT and stirred at RT for 2 hours. The reaction was quenched by addition of sat. aqueous solution of K2CO3, and the resulting mixture was extracted with DCM (20 mL×3). The combined organic layers were dried over Na2SO4, and then concentrated in vacuo to afford the crude benzyl 6-oxabicyclo[3.1.0]hex-3-ylcarbamate (1.5 g), which was used in the next step directly.

Workup

  1. customThe reaction was quenched by addition of sat. aqueous solution of K2CO3
  2. extractionthe resulting mixture was extracted with DCM (20 mL×3)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6e47dd6540cc4e14b501fa87b92f79ec
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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