Nitromethane → 1-Amino-4-phenylbutan-2-ol

HRID 21365

Reaktionsgleichung

Reaktionsgleichung von HRID 21365
[CH:1](=[O:10])[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[N+:11]([CH3:14])([O-])=O.CN(C)C(=N)N(C)C>C(O)C>[CH:7]1[CH:8]=[CH:9][C:4]([CH2:3][CH2:2][CH:1]([OH:10])[CH2:14][NH2:11])=[CH:5][CH:6]=1

Komponenten

5

Edukt 3

HCID 6375NitromethaneHCID 7707BenzenepropanalHCID 664601,1,3,3-Tetramethylguanidine

Produkt 1

HCID 157609871-Amino-4-phenylbutan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

6.70 g of dihydrocinnamaldehyde are dissolved in 20 ml of anhydrous ethanol, and 10 ml of nitromethane and 1 ml of tetramethylguanidine are added, and the mixture is stirred at RT for 1 h. It is concentrated in vacuo, the residue is taken up in 200 ml of ethanol and 5 ml of glacial acetic acid, 10 g of activated Raney nickel are added and the mixture is then hydrogenated at 50° C. and under 25 bar H2 pressure for 5 h. The catalyst is then filtered off, the filtrate is concentrated in vacuo, the residue is taken up in saturated aqueous sodium bicarbonate solution, and non-polar impurities are removed by extraction with diethyl ether. Extraction 3 times with tetrahydrofuran, drying over sodium sulfate, and concentration in vacuo provides 5.75 g of (D,L)-4-phenyl-2-hydroxy-1-butylamine as a colorless oil.

Aufarbeitung

  1. concentrationIt is concentrated in vacuo
  2. addition5 ml of glacial acetic acid, 10 g of activated Raney nickel are added
  3. waitthe mixture is then hydrogenated at 50° C. and under 25 bar H2 pressure for 5 h
  4. filtrationThe catalyst is then filtered off
  5. concentrationthe filtrate is concentrated in vacuo
  6. customnon-polar impurities are removed by extraction with diethyl ether
  7. extractionExtraction 3 times with tetrahydrofuran
  8. dry with materialdrying over sodium sulfate, and concentration in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f90ea99ce0d34af69324ce3bf2b03ac9
Quelldatensatz
uspto-grants-1995_06
Patentnummer
US05422342

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