Water → Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate

HRID 658264

Reaktionsgleichung

Reaktionsgleichung von HRID 658264
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[BH4-].[Na+].[NH4+].[Cl-].O>CO>[OH:2][CH2:1][C@@H:3]1[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7]

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 4311764Sodium borohydride

Produkt 1

HCID 29920784Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of ethyl 2-formyl-1-cyclopropanecarboxylate (1.5 eq.) in methanol (0.7 M) at 0° C. was added sodium borohydride (1.5 eq.) in portions over 30 min. The mixture was allowed to stir at rt for 1.5 h and then cooled in an ice bath. Saturated aqueous NH4Cl solution was added dropwise, and the mixture was stirred for 1.5 h. Water was added, and the aqueous layer was extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4, and concentrated to afford a racemic mixture of the title compound as a clear oil. Racemic trans 2-(hydroxymethyl)cyclopropanecarboxylate was purified by a Chiral Pak AD preparative column (10% EtOH/Hex) to afford two enantiomers. Ethyl (1R,2R)-2-(hydroxymethyl)cyclopropanecarboxylate was eluted as the faster enantiomer (retention time=12.94 min).

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. stirringthe mixture was stirred for 1.5 h
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-481c4fb409f34d669adb731adb461764
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08076359B2

Verknüpfte Notizen

Wird geladen…