Chloride → 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one

HRID 271249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 271249
[O:1]1[CH2:3][C@@H:2]1[CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1.[NH:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1.[Cl-].C(N(C(C)C)CC)(C)C>C(O)C>[OH:1][C@@H:2]([CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([CH3:14])=[N:11][C:10]=2[CH:15]=1)[CH2:3][N:16]1[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]1

Komponenten

6

Edukt 4

HCID 312ChlorideHCID 337214-PiperidoneHCID 81531DiisopropylethylamineHCID 210236065-(((R)-oxiran-2-yl)methoxy)-2-methylbenzo[d]thiazole

Produkt 1

HCID 587143351-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 5-[((2R)oxiran-2-yl)methoxy]-2-methylbenzothiazole (2.0 g, 9.25 mmol) and piperidin-4-one, chloride (1.25 g, 9.25 mmol) in ethanol was added diisopropylethylamine (1.6 ml, 9.0 mmol). The mixture was heated to reflux for 16 hours. The solvent was removed and the residue purified by column chromatography (10:1 DCM:MeOH) followed by preparative TLC (10:1 DCM:MeOH) to yield 1-[(2R)-2-hydroxy-3-(2-methylbenzothiazol-5-yloxy)propyl]piperidin-4-one.

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 16 hours
  3. customThe solvent was removed
  4. customthe residue purified by column chromatography (10:1 DCM:MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-63229c9e639d4418bc595bd7232a6e9d
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452889B2

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