HCID 22329264, compound → HCID 22329067, compound

HRID 586922Notes

Reaction equation

HRID 586922 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH:19]2[CH2:21][CH2:20]2)[CH2:9][CH2:10][CH2:11][C:12]([O:14]C(C)(C)C)=[O:13])=[C:4]([CH:22]=O)[CH:3]=1.CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]([CH:19]3[CH2:20][CH2:21]3)[CH2:9][CH2:10][C:11]([C:12]([OH:14])=[O:13])=[CH:22][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 22329264HCID 22329264, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22329067HCID 22329067, compoundYield 54.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
55 °C

Procedure

In THF (10 ml) was dissolved t-butyl N-(4-bromo-2-formylphenyl)-N-cyclopropyl-4-aminobutyrate (1 g). To the solution was added potassium t-butoxide (0.59 g), and the mixture was heated at 55° C. for 1.5 hours. The solvent was evaporated, which was extracted with water. The aqueous layer was washed with ethyl acetate, and neutralized by addition of 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with anhydrous magnesium sulfate. The solvent was evaporated to give 7-bromo-1-cyclopropyl-2,3-dihydro-1H-1-benzazepine-4-carboxylic acid (0.44 g) as yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. extractionwhich was extracted with water
  3. washThe aqueous layer was washed with ethyl acetate
  4. additionneutralized by addition of 1N hydrochloric acid
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customThe solvent was evaporated

Sources & evidence

ORD record
ord-d056abadc9d64fcfa29329e5ad0d686b
Source dataset
uspto-grants-2005_08
Patent number
US06936602B1

Reaction notes

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