Methanol → 2-[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]ethanol

HRID 1612891Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1612891
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][C:22](O)=[O:23])[CH:18]=3)[CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]2[CH2:20][C:19]3[C:14](=[CH:15][CH:16]=[C:17]([CH2:21][CH2:22][OH:23])[CH:18]=3)[CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 163920SX-AB 1316 SE

Produkt 1

HCID 151244462-[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]ethanolAusbeute 93,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

[2-[(4-Chlorophenyl)sulfonylamino]indan-5-yl]acetic acid (600 mg) is dissolved in tetrahydrofuran (20 ml) and thereto is added dropwise 7.8M borane-1,4-oxathiane complex (1 ml). The mixture is stirred at room temperature for one hour and thereto is added methanol to terminate the reaction, and then, the solvent is distilled off under reduced pressure. The residue is dissolved in ethyl acetate and washed with aqueous sodium hydrogen carbonate solution and saline solution, dried and then distilled under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent, chloroform) to give 2-[2-[(4-chlorophenyl)sulfonylamino]indan-5-yl]ethanol (542 mg) as colorless crystals.

Aufarbeitung

  1. additionis added dropwise 7.8M borane-1,4-oxathiane complex (1 ml)
  2. customto terminate
  3. customthe reaction
  4. distillationthe solvent is distilled off under reduced pressure
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed with aqueous sodium hydrogen carbonate solution and saline solution
  7. customdried
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent, chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-7bbada0fd0954f63b0bea77e25257c1b
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05190975

Notizen zur Reaktion

Wird geladen…