Hydrochloric Acid → (2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride

HRID 333193

Reaktionsgleichung

Reaktionsgleichung von HRID 333193
[CH3:1][N:2]([CH3:18])[CH2:3][C@H:4]([CH3:17])[C@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([OH:8])[CH2:6][CH3:7].B(O)(O)[C@H]1N(C([C@@H](N)C(C)C)=O)CCC1.CS(O)(=O)=O.[ClH:39]>CC(C)=O>[ClH:39].[CH3:18][N:2]([CH3:1])[CH2:3][C@H:4]([CH3:17])[C@:5]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[CH:10]=1)([OH:8])[CH2:6][CH3:7]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 9942979(alphaR)-alpha-[(1S)-2-(Dimethylamino)-1-methylethyl]-alpha-ethyl-3-methoxybenzenemethanolHCID 11522448Talabostat mesylate

Produkt 1

HCID 25146677(2S,3R)-1-(dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

(2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol (754.1 g, 3 mol, ee 95%) were dissolved in acetone (5 L) in a 10 L double jacket vessel equipped with an electrical impeller stirrer, a gas transition line, Pt100 temperature measuring equipment and an oil based cooling/heating system. Hydrogen chloride (110 g, 3.0 mol) was transferred within 15 minutes at a temperature of 15° C. through the reaction mixture. The reaction mixture was cooled to 0° C. to 5° C. and after 24 hours at that temperature siphoned off. The product was stored at 40° C. and 10 mbar for 14 hours in a drying oven. (2S,3R)-1-(Dimethylamino)-3-(3-methoxyphenyl)-2-methylpentan-3-ol hydrochloride was obtained as a colorless solid (722.3 g, 83.7%, ee 100%).

Aufarbeitung

  1. customequipped with an electrical impeller stirrer
  2. temperatureThe reaction mixture was cooled to 0° C. to 5° C. and after 24 hours at that temperature
  3. customwas stored at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-cad94cb148f243ecaae573cd2e83d2bd
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08877974B2

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