Triethylamine → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 12401

Reaktionsgleichung

Reaktionsgleichung von HRID 12401
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](O)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.ClC(OCC)=O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-

Produkt 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanolAusbeute 89,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

O-benzyl-N-(t-butoxycarbonyl)-L-serine (2 g) was dissolved in tetrahydrofuran (20 ml), triethylamine (1.22 ml) was added, and ethyl chloroformate (713 μl) was further added dropwise at 0° C. After stirring the reaction mixture at room temperature for 30 min, the reaction mixture was filtered, and one piece of ice was added to the filtrate. Sodium borohydride (515 mg) was further added, and the mixture was stirred at room temperature for 6 hrs. The reaction mixture was diluted with ethyl acetate and, after washing with water, the organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained crude product was purified by silica gel chromatography (ethyl acetate-hexane) to give t-butyl (1R)-2-(benzyloxy)-1-(hydroxymethyl)ethylcarbamate (1.7 g)

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. additionone piece of ice was added to the filtrate
  3. additionSodium borohydride (515 mg) was further added
  4. stirringthe mixture was stirred at room temperature for 6 hrs
  5. additionThe reaction mixture was diluted with ethyl acetate
  6. washafter washing with water
  7. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  8. customThe solvent was evaporated
  9. customthe obtained crude product
  10. customwas purified by silica gel chromatography (ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-62c17d1cfb3e4e06b586c994edd4847a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07728005B2

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