Hydrochloric Acid → (S)-(+)-2-Indolinemethanol

HRID 2059887Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059887
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[C:10](O)=[O:11].CO.Cl>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C@H:2]1[CH2:10][OH:11]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 2733920Indoline-2-carboxylic acid, (S)-

Produkt 1

HCID 6951186(S)-(+)-2-IndolinemethanolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

BH3-DMS solution (18.4 mmol, 2 eq) was added dropwise to a solution of (S)-indoline-2-carboxylic acid (9.2 mmol, 1.0 eq) in THF (18 ml) and the mixture was refluxed for 12 h. Methanol (7.5 ml) and concentrated HCl (2.5 ml) were added to the reaction mixture with cooling, then refluxing was continued for a further 2 hours. The solvent was removed under vacuum and the residue made alkaline with 40% NaOH solution and extracted with DCM. The organic phase was washed with saturated sodium chloride solution, dried (Na2SO4) and concentrated to small volume under vacuum. The crude product was processed by column chromatography. Yield: 87%

Aufarbeitung

  1. temperaturethe mixture was refluxed for 12 h
  2. temperaturewith cooling
  3. temperaturerefluxing
  4. customThe solvent was removed under vacuum
  5. extractionextracted with DCM
  6. washThe organic phase was washed with saturated sodium chloride solution
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated to small volume under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-d8546a675bad4e3195efa0d0e353c384
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08278319B2

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