Sodium borohydride → tert-Butyl cyclopropanecarboxylate

HRID 130615

Reaktionsgleichung

Reaktionsgleichung von HRID 130615
[BH4-].[Na+].Cl[C:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1>CN(C)C(=O)C.O.O.O.O.O.O.[Co](Cl)Cl>[CH:4]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5]1

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 23158972Tert-butyl 1-chlorocyclopropane-1-carboxylate

Produkt 1

HCID 13676038tert-Butyl cyclopropanecarboxylateAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 517166Dichlorocobalt hexahydrateKatalysatorHCID 31374DimethylacetamideLösungsmittel2×

Versuchsvorschrift

Sodium borohydride (161 mg, 4.25 mmol) was added to and dissolved in N,N-dimethylacetamide (1.5 mL) at room temperature, followed by addition of an N,N-dimethylacetamide solution (1.0 mL) of tert-butyl 1-chlorocyclopropane-1-carboxylate (hereinafter the compound will be referred to as “compound (4a)”) (500 mg, 2.83 mmol) at 10C. Cobalt chloride hexahydrate (3.3 mg, 0.014 mmol) was added to the resultant solution. After completion of addition, the resultant mixture was stirred at 40° C. for 21 hours. After completion of reaction, the whole reaction mixture was diluted with an HPLC mobile phase to 50 mL, to thereby yield a solution containing 320.3 mg (yield: 80%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).

Aufarbeitung

  1. additionAfter completion of addition
  2. customAfter completion of reaction
  3. customthe whole reaction mixture
  4. additionwas diluted with an HPLC mobile phase to 50 mL
  5. customto thereby yield a solution

Quellen und Nachweise

ORD-Eintrag
ord-d6502d67816c4188a96ba01742d41619
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381833B2

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