m-Chloroperbenzoic acid → HCID 59032948, compound

HRID 1634716Notes

Reaction equation

HRID 1634716 reaction equation
[O:1]1[CH2:3][C@H:2]1[CH2:4][O:5][C:6]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.ClC1C=CC=C(C(OO)=[O:27])C=1>C(Cl)Cl>[OH:27][C:7]1[CH:8]=[CH:9][C:10]2[NH:11][C:12]3[C:17]([C:18]=2[C:6]=1[O:5][CH2:4][C@@H:2]1[CH2:3][O:1]1)=[CH:16][CH:15]=[CH:14][CH:13]=3

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 10879208(S)-(+)-4-(2,3-Epoxypropoxy)carbazole

Product 1

HCID 59032948HCID 59032948, compoundYield 20.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-[(2S)-oxiranylmethoxy]-9H-carbazole (0.183 g, 0.76 mmol) in 20 mL dry methylene chloride was treated with 0.258 g of 56-86% m-chloroperbenzoic acid. The reaction was stirred at ambient temperature for 45 minutes. The reaction mixture was partitioned with saturated sodium bicarbonate (sat'd NaHCO3) The organic phase was dried (Na2SO4) and concentrated to a dark red oil. Purification by flash chromatography eluting with methylene chloride (CH2Cl2), afforded 0.040 g of the title compound.

Workup

  1. customThe reaction mixture was partitioned with saturated sodium bicarbonate (sat'd NaHCO3) The organic phase
  2. dry with materialwas dried (Na2SO4)
  3. concentrationconcentrated to a dark red oil
  4. customPurification by flash chromatography
  5. washeluting with methylene chloride (CH2Cl2)

Sources & evidence

ORD record
ord-46857b66505c4a4b8c4d710c4e23fa0a
Source dataset
uspto-grants-2003_01
Patent number
US06506901B2

Reaction notes

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