Acetic Acid → 4-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

HRID 470408Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 470408
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH2:10])[CH3:9])=[CH:4][CH:3]=1.C(O)(=O)C.[OH:15][C:16]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([CH2:20][O:21][CH3:22])[CH2:17][CH:18]=O>O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][CH2:18][CH2:17][C:16]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([OH:15])[CH2:20][O:21][CH3:22])[CH3:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 852999(alphaS)-4-Bromo-alpha-methylbenzenemethanamineHCID 596356773-Hydroxy-4-methoxy-3-phenyl-butyraldehyde

Produkt 1

HCID 596357994-[(S)-1-(4-Bromo-phenyl)-ethylamino]-1-methoxy-2-phenyl-butan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

(S)-1-(4-Bromo-phenyl)-ethylamine (0.93 g), NaB(OAc)3 (0.98 g), and acetic acid (0.27 mL) were added in the given order to a solution of 3-hydroxy-4-methoxy-3-phenyl-butyraldehyde (0.90 g) in tetrahydrofuran (20 mL) at ca. 10-15° C. The cooling bath was removed and the mixture was stirred at room temperature for 2 h. Then, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added and the resulting mixture was stirred for another 30 min. The mixture was extracted with ethyl acetate and the combined extracts were washed with water and brine. After drying (MgSO4), the solvent was removed to give the title compound which was submitted to the subsequent reaction step without further purification. Yield: 1.80 g (quantitative).

Aufarbeitung

  1. customThe cooling bath was removed
  2. additionThen, water (50 mL) and 1 M aqueous NaOH solution (20 mL) were added
  3. stirringthe resulting mixture was stirred for another 30 min
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe combined extracts were washed with water and brine
  6. dry with materialAfter drying (MgSO4)
  7. customthe solvent was removed

Quellen und Nachweise

ORD-Eintrag
ord-87e1f83152c54fa0bba0099047097100
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08629138B2

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