Borane;tetrahydrofuran → HCID 66780431, compound

HRID 406394Notes

Reaction equation

HRID 406394 reaction equation
B.C1COCC1.[Cl:7][C:8]1[CH:17]=[C:16]([N:18]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[C:19](=O)[C:20]([F:23])([F:22])[F:21])[CH:15]=[CH:14][C:9]=1[C:10](OC)=[O:11]>ClCCl.O>[Cl:7][C:8]1[CH:17]=[C:16]([N:18]([CH2:25][CH:26]2[CH2:28][CH2:27]2)[CH2:19][C:20]([F:22])([F:23])[F:21])[CH:15]=[CH:14][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 86662654HCID 86662654, compound

Product 1

HCID 66780431HCID 66780431, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Borane-THF complex (1.0M solution in THF, 13.7 ml) was added under ice-cooling to a solution of methyl 2-chloro-4-[cyclopropylmethyl(2,2,2-trifluoroacetyl)amino]benzoate (500 mg) in dichloromethane (10 ml). The reaction mixture was then refluxed overnight. After cooling to room temperature, the mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate.

Workup

  1. temperatureThe reaction mixture was then refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-279ab1ab58fd47eaa1330f85fc24eca7
Source dataset
uspto-grants-2014_06
Patent number
US08754100B2

Reaction notes

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