HCID 131727232, compound → (1S)-1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one

HRID 2376622Notes

Reaction equation

HRID 2376622 reaction equation
C1(C)C=CC(C([C@@](C(O)=O)(O)[C@@](C(C2C=CC(C)=CC=2)=O)(O)C(O)=O)=O)=CC=1.[NH2:29][C@H:30]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH2:34][CH2:33][N:32]([CH3:41])[C:31]1=[O:42]>[OH-].[Na+]>[NH2:29][C@H:30]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[CH2:34][CH2:33][N:32]([CH3:41])[C:31]1=[O:42]

Participants

3

Reactant 1

HCID 131727232HCID 131727232, compound

Product 1

HCID 44178390(1S)-1-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneYield 87%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

(S)-1-Amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one di-p-toluoyl-L-tartaric acid salt (11.83 g, 20.5 mmol) was dissolved in 45 mL of aqueous 1.0 N sodium hydroxide solution and extracted with methylene chloride (3×25 mL). The combined methylene chloride layers were washed with 35 mL aqueous 1.0 N sodium hydroxide solution, then brine solution, and dried over anhydrous MgSO4. Removal of solvent under vacuum gave the title compound (3.38 g) as a colorless oil (87% yield, 93.2% ee).

Workup

  1. extractionextracted with methylene chloride (3×25 mL)
  2. washThe combined methylene chloride layers were washed with 35 mL aqueous 1.0 N sodium hydroxide solution
  3. dry with materialbrine solution, and dried over anhydrous MgSO4
  4. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-32d9c7747be54b71a727ce71a3c32995
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

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