Triethylamine → (S)-N-CBZ-valinol

HRID 326536

Reaktionsgleichung

Reaktionsgleichung von HRID 326536
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[NH2:12][C@H:13]([CH2:17][OH:18])[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([NH:12][C@H:13]([CH2:17][OH:18])[CH:14]([CH3:16])[CH3:15])=[O:3])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

Produkt 1

HCID 10900657(S)-N-CBZ-valinolAusbeute 79,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Benzyl chloroformate (91.0 g, 95% purity) was added dropwise over a period of 1 h to a precooled (0° C.) solution of L-valinol (50.0 g) and triethylamine (60.0 g) in chloroform (1500 ml). The reaction mixture was stirred for 1 h at 0° C. and then allowed to warm to,room temperature over 2 h. After the reaction mixture was evaporated, ethyl acetate (1500 ml) was added to the residue and the organic solution was washed (1N NaOH, brine), dried (MgSO4), and evaporated. The residue was purified by flash chromatography, using a stepwise gradient elution of ether:hexane (1:5) followed by ether, to give the alcohol (91.4 g) as a white waxy solid; TLC, Rf =0.23, hexane:ethanol (50:50).

Aufarbeitung

  1. temperatureto warm to,room temperature over 2 h
  2. customAfter the reaction mixture was evaporated
  3. additionethyl acetate (1500 ml) was added to the residue
  4. washthe organic solution was washed (1N NaOH, brine)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe residue was purified by flash chromatography
  8. washa stepwise gradient elution of ether:hexane (1:5)

Quellen und Nachweise

ORD-Eintrag
ord-3f551c17853f43e9992170149f9e5f33
Quelldatensatz
uspto-grants-1993_12
Patentnummer
US05270301

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