Sodium borohydride → N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide

HRID 1894768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1894768
[CH2:1]([CH:3]([CH2:16][CH3:17])[C:4]([C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[BH4-].[Na+]>CO>[CH2:16]([CH:3]([CH2:1][CH3:2])[CH:4]([C:6]1[CH:7]=[CH:8][C:9]([NH:12][C:13](=[O:15])[CH3:14])=[CH:10][CH:11]=1)[OH:5])[CH3:17]

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 43160160N-(4-(2-ethylbutanoyl)phenyl)acetamide

Produkt 1

HCID 22603035N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of N-(4-(2-ethylbutanoyl)phenyl)acetamide (730 mg, 3.13 mmol) in MeOH (20 mL) was cooled in an ice bath under N2 and treated with NaBH4 (148 mg, 3.91 mmol), added in one portion. The reaction vessel was removed from the ice bath and stirred overnight at RT. The reaction was concentrated and partitioned between DCM and half-saturated NaHCO3. The aqueous phase was extracted four times with DCM and the organic extracts were combined and dried over MgSO4, filtered and then concentrated. The crude product was purified by preparative TLC using 50% ethyl acetate in hexane as eluent to afford N-(4-(2-ethyl-1-hydroxybutyl)phenyl)acetamide as white solid. MS (ES+): m/z 236.24 (MH+).

Aufarbeitung

  1. additionadded in one portion
  2. customThe reaction vessel was removed from the ice bath
  3. concentrationThe reaction was concentrated
  4. custompartitioned between DCM and half-saturated NaHCO3
  5. extractionThe aqueous phase was extracted four times with DCM
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-fad7472522a44a378bd3135c57be45f1
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513291B2

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