Hydrochloric Acid → Tert-butyl 2-fluoro-cyclopropane-1-carboxylate

HRID 130612

Reaktionsgleichung

Reaktionsgleichung von HRID 130612
[BH4-].[Na+].Cl[C:4]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH:5]1[F:7].O.Cl>CN1C(=O)CCC1.O.O.O.O.O.O.[Co](Cl)Cl.C1(C)C=CC=CC=1>[F:7][CH:5]1[CH2:6][CH:4]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4311764Sodium borohydrideHCID 11858685Tert-butyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate

Produkt 1

HCID 11819326Tert-butyl 2-fluoro-cyclopropane-1-carboxylateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 517166Dichlorocobalt hexahydrateKatalysatorHCID 1140TolueneLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel3×

Versuchsvorschrift

Sodium borohydride (8.75 g, 231.21 mmol) was dissolved in NMP (95 mL) under stirring with a stirring blade at room temperature. Subsequently, to the resultant solution was added an NMP solution (20 mL) of tert-butyl 1-chloro-2-fluoro-cyclopropane-1-carboxylate (cis/trans=62/38) (hereinafter the compound will be referred to as “compound (1a)”) (30 g, 154.14 mmol). An NMP solution (35 mL) of cobalt chloride hexahydrate (1.1 g, 4.62 mmol) was gradually added to the resultant reaction mixture under ice cooling. After completion of dropwise addition, the resultant mixture was stirred with a stirring blade at room temperature for 30 minutes, and at 40° C. for three hours. After completion of reaction, water (120 mL) was added to the resultant reaction mixture at the same temperature, followed by addition of 5 N hydrochloric acid (30 mL). Subsequently, toluene was added to the reaction mixture for extraction. The resultant toluene layer was washed with water, and then dried over sodium sulfate, to thereby yield a toluene solution containing 24.3 g (yield: 98%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).

Aufarbeitung

  1. customreaction mixture under ice cooling
  2. additionAfter completion of dropwise addition
  3. additionwas added to the resultant
  4. customreaction mixture at the same temperature
  5. washThe resultant toluene layer was washed with water
  6. dry with materialdried over sodium sulfate
  7. customto thereby yield a toluene solution

Quellen und Nachweise

ORD-Eintrag
ord-31dde147dee64b16bd0a80d7ce46349c
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07381833B2

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