Sodium Hydroxide → HCID 58495329, compound

HRID 516244Notes

Reaction equation

HRID 516244 reaction equation
[OH:1][C:2]1[C:3]([C:20](=[O:22])[CH3:21])=[CH:4][C:5]2[CH:11]([CH3:12])[CH2:10][N:9]([C:13](=[O:18])C(F)(F)F)[CH2:8][CH2:7][C:6]=2[CH:19]=1.[OH-:23].[Na+]>CO>[C:20]([C:3]1[C:2]([OH:1])=[CH:19][C:6]2[CH2:7][CH2:8][N:9]([C:13]([O:23][C:3]([CH3:20])([CH3:4])[CH3:2])=[O:18])[CH2:10][CH:11]([CH3:12])[C:5]=2[CH:4]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58494928HCID 58494928, compound

Product 1

HCID 58495329HCID 58495329, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 5.13 g of 1-[8-hydroxy-5-methyl-3-(trifluoroacetyl)-2,3,4,5-tetrahydro-1H-3-benzazepine-7-yl]ethanone in 50 ml of MeOH was added 50 ml of a 1 M aqueous sodium hydroxide solution, followed by stirring at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure to a half of the amount, and to the residue were added 50 ml of dioxane and 4.27 g of di-t-butyl dicarbonate, followed by stirring at room temperature for 30 minutes. The reaction mixture was neutralized by the addition of 1 M hydrochloric acid and extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 4.385 g of t-butyl 8-acetyl-7-hydroxy-1-methyl-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate as a yellow viscous substance.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure to a half of the amount
  2. additionto the residue were added 50 ml of dioxane and 4.27 g of di-t-butyl dicarbonate
  3. stirringby stirring at room temperature for 30 minutes
  4. additionThe reaction mixture was neutralized by the addition of 1 M hydrochloric acid
  5. extractionextracted with chloroform
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-c8d2f615a9c64d23add3dff021e8098a
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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