2-Amino-2-methyl-1-propanol → (2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol

HRID 24274

Reaktionsgleichung

Reaktionsgleichung von HRID 24274
Br[CH:2]([CH3:12])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)=[O:4].[NH2:13][C:14]([CH3:18])([CH3:17])[CH2:15][OH:16]>CO>[Cl:11][C:7]1[CH:6]=[C:5]([C@@:3]2([OH:4])[O:16][CH2:15][C:14]([CH3:18])([CH3:17])[NH:13][C@@H:2]2[CH3:12])[CH:10]=[CH:9][CH:8]=1

Komponenten

4

Edukt 2

HCID 118072-Amino-2-methyl-1-propanolHCID 4992116alpha-Bromo-3-chloropropiophenone

Produkt 1

HCID 9943908(2R,3R)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinolAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 2-bromo-3′-chloropropiophenone (19.3 g, 0.08 mol) in MeOH (100 mL) was added dropwise a solution of 2-amino-2-methyl-1-propanol (27.8 g, 0.31 mol) in methanol (200 mL) at ambient temperature. The mixture was stirred for 18 h and concentrated in vacuo. The residue was partitioned between water and diethyl ether. The combined organic phase was extracted with 10% aqueous hydrogen chloride. The combined aqueous acid extracts were chilled in an ice bath and made basic with 40% aqueous sodium hydroxide. The mixture was extracted with diethyl ether, the combined diethyl ether extracts were washed with water and saturated sodium chloride solution, dried (K2CO3) and concentrated in vacuo to give 15.0 g (75%) of (+/−)-(2R*,3R*)-2-(3-chlorophenyl)-3,5,5-trimethyl-2-morpholinol as an off-white solid.

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between water and diethyl ether
  3. extractionThe combined organic phase was extracted with 10% aqueous hydrogen chloride
  4. temperatureThe combined aqueous acid extracts were chilled in an ice bath
  5. extractionThe mixture was extracted with diethyl ether
  6. washthe combined diethyl ether extracts were washed with water and saturated sodium chloride solution
  7. dry with materialdried (K2CO3)
  8. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-face969c0b2245dd9ec31f7e2055c39c
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06855820B2

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