Hydrochloric Acid → N-Tosylhydroxy-L-prolinol

HRID 1031485

Reaktionsgleichung

Reaktionsgleichung von HRID 1031485
C[O:2][C:3](=O)[C@:4]1([OH:19])[CH2:8][CH2:7][CH2:6][N:5]1[S:9]([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].Cl>C1COCC1>[S:9]([N:5]1[CH2:6][CH2:7][CH2:8][C@@:4]1([OH:19])[CH2:3][OH:2])([C:12]1[CH:13]=[CH:14][C:15]([CH3:16])=[CH:17][CH:18]=1)(=[O:10])=[O:11]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 18640953N-tosylhydroxy-L-proline methyl ester

Produkt 1

HCID 67796897N-Tosylhydroxy-L-prolinolAusbeute 89,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

To a solution of N-tosylhydroxy-L-proline methyl ester (62.20 g) in THF (600 mL) at 0° C. for 1 h and allowed to stand at 23° C. for 18 h. The reaction mixture was cooled to -20° C., made neutral with 6N HCl, and concentrated under reduced pressure. The residue was treated with water (550 mL) and extracted with EtOAc (4×300 mL). The combined organic extracts were washed with H2O, dried over MgSO4, filtered, and concentrated under reduced pressure to give N-tosylhydroxy-L-prolinol as a white solid (50.56 g, 88.8%) which was used in the next step without further purification.

Aufarbeitung

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was treated with water (550 mL)
  3. extractionextracted with EtOAc (4×300 mL)
  4. washThe combined organic extracts were washed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-402ca228848c47c49fd7f2464c23d2ae
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04954502

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