Borane → (S)-2-(p-toluenesulfonylamino)-1,4-butanediol

HRID 1655634Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1655634
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([S:7]([NH:10][C@H:11]([C:16](O)=[O:17])[CH2:12][C:13](O)=[O:14])(=[O:9])=[O:8])=[CH:3][CH:2]=1.B>O1CCCC1.CO>[C:1]1([CH3:19])[CH:2]=[CH:3][C:4]([S:7]([NH:10][C@@H:11]([CH2:12][CH2:13][OH:14])[CH2:16][OH:17])(=[O:9])=[O:8])=[CH:5][CH:6]=1

Komponenten

5

Edukt 2

HCID 6331BoraneHCID 107597N-tosyl-L-aspartic acid

Produkt 1

HCID 10934189(S)-2-(p-toluenesulfonylamino)-1,4-butanediol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

N-(p-Toluenesulfonyl)-L-aspartic acid, 1, (110 g) was dissolved in tetrahydrofuran (300 mL) and the solution cooled to -5° C. under a nitrogen atmosphere. A 1.0M solution of borane in tetrahydrofuran was added dropwise over 1 hour at 0 to -5° C. and the resulting solution stirred at 20° to 25° C. overnight. The solution was recooled to 0° C. and methanol (250 mL) was added dropwise over 30 minutes (caution! gas evolution). The solution was concentrated under vacuum to an oil which was redissolved in methanol (1L) and the solution heated at reflux 1 hour. This solution was concentrated under vacuum to give a solid which was redissolved in methanol (1L) and this solution heated at reflux for 2 hours. Finally the solution was concentrated to a solid which was dried under vacuum at 50° C. to give (S)-2-(p-toluenesulfonylamino)-1,4-butanediol, 2, as an off white solid (97 g, 98%) which was used directly in the next step without further purification. A portion was recrystallized from isopropyl alcohol and hexanes: mp 90°-92° C.

Aufarbeitung

  1. customwas recooled to 0° C.
  2. concentrationThe solution was concentrated under vacuum to an oil which
  3. dissolutionwas redissolved in methanol (1L)
  4. temperaturethe solution heated
  5. temperatureat reflux 1 hour
  6. concentrationThis solution was concentrated under vacuum
  7. customto give a solid which
  8. temperaturethis solution heated
  9. temperatureat reflux for 2 hours
  10. concentrationFinally the solution was concentrated to a solid which
  11. customwas dried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-902c609923024499bb241cb91199fed0
Quelldatensatz
uspto-grants-1993_10
Patentnummer
US05250704

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