Triethylamine → (S)-N-CBZ-valinol

HRID 53113

Reaktionsgleichung

Reaktionsgleichung von HRID 53113
[NH2:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4].C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C(Cl)Cl>[CH2:19]([O:18][C:16]([NH:1][C@H:2]([CH2:6][OH:7])[CH:3]([CH3:5])[CH3:4])=[O:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 640993L-Valinol

Produkt 1

HCID 10900657(S)-N-CBZ-valinolAusbeute 95,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a stirred solution of valinol (13.96 g, 0.14 mol) and triethylamine (18.87 mL, 0.14 mol) in 250 mL of dry methylene chloride cooled to 0° C. under a nitrogen atmosphere was added 19.3 mL (0.14 mol) of benzyl chloroformate dropwise over 20 min. After warming to RT overnight, the mixture was diluted with methylene chloride (100 mL) and washed with 1N HCl (2×), brine and dried with anhydrous magnesium sulfate. The resulting mixture was filtered and evaporated to give 30.70 g (95.6%) of N-benzyloxycarbonyl-valinol as a white solid: Rf =0.27 (silica gel; 1:1 hexane:ethyl acetate). Used without further purification.

Aufarbeitung

  1. washwashed with 1N HCl (2×), brine
  2. dry with materialdried with anhydrous magnesium sulfate
  3. filtrationThe resulting mixture was filtered
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-07d3e2fb476846c98aa15dff4b0ec5d4
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05618792

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