m-Chloroperbenzoic acid → 1'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxide

HRID 1275146Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275146
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[OH:23].[Na+].ClC1C=CC=C(C(OO)=O)C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][S:14]2=[O:23])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10566517HCID 10566517, Verbindung

Produkt 1

HCID 107345601'-t-Butoxycarbonylspiro[benzo[c]thiophene-1-(3H),4'-piperidine]-2-oxideAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

485 mg (1.59 mmole) of 1'-t-butoxycarbonylspiro[benzo[c]thiophene-1(3H),4'-piperidine] [prepared as described in Preparation 3(b)] were dissolved in 5 ml of anhydrous methylene chloride, and 148 mg (1.76 mmole) of sodium hydrogencarbonate were added, followed by 325 mg (1.88 mmole, content: 85%) of m-chloroperbenzoic acid, whilst ice-cooling. The reaction mixture was stirred whilst ice-cooling, for 30 minutes, after which it was diluted with methylene chloride and then washed, in turn, with water and with a saturated aqueous solution of sodium chloride. The solution was dried over anhydrous sodium sulfate, and then the solvent was removed by distillation under reduced pressure, and the resulting residue was purified by thin-layer chromatography, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent, to give 498 mg (yield 98%) of the title compound as white crystals.

Aufarbeitung

  1. temperaturecooling
  2. temperaturecooling, for 30 minutes
  3. washwashed, in turn, with water and with a saturated aqueous solution of sodium chloride
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customthe resulting residue was purified by thin-layer chromatography
  7. additionby volume mixture of ethyl acetate and hexane as the developing solvent

Quellen und Nachweise

ORD-Eintrag
ord-11afef4e38a141bda6e870e91398bddb
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06159967

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