Sodium borohydride → Tert-butyl 2-fluoro-cyclopropane-1-carboxylate

HRID 130614Notes

Reaction equation

HRID 130614 reaction equation
[BH4-].[Na+].Cl[C:4]1([F:14])[CH2:6][CH:5]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]>CN(C)C(=O)C.[Co](Cl)Cl>[F:14][CH:4]1[CH2:6][CH:5]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 23158973Tert-butyl 2-chloro-2-fluoro-cyclopropane-1-carboxylate

Product 1

HCID 11819326Tert-butyl 2-fluoro-cyclopropane-1-carboxylateYield 84%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 31374DimethylacetamideSolvent2×

Procedure

Sodium borohydride (243 mg, 6.43 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 2-chloro-2-fluoro-cyclopropane-1-carboxylate (cis/trans=57/43) (hereinafter the compound will be referred to as “compound (1d)”) (500 mg, 2.57 mmol). Cobalt chloride (33.4 mg, 1.54 mmol) was added to the resultant solution. After completion of addition, the resultant mixture was stirred at 50° C. for 14 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 344.6 mg (yield: 84%) of the title compound. Yield was determined by means of high performance liquid chromatography (HPLC) (the same shall apply hereinafter).

Workup

  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

Sources & evidence

ORD record
ord-8e19d848413f495c849d3bf9a1b17137
Source dataset
uspto-grants-2008_06
Patent number
US07381833B2

Reaction notes

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