Ammonium Chloride → HCID 86692531, compound

HRID 1748579Notes

Reaction equation

HRID 1748579 reaction equation
Br[C:2]1[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.C([Li])CCC.[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][C:25](=[O:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:17])[CH3:16].[Cl-].[NH4+]>C1(C)C=CC=CC=1.CCCCCC>[C:15]([O:19][C:20]([N:22]1[CH2:28][CH2:27][CH2:26][C:25]([C:2]2[C:7]([CH3:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=2)([OH:29])[CH2:24][CH2:23]1)=[O:21])([CH3:18])([CH3:16])[CH3:17]

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 8176802,5-Dibromo-3-methylpyridineHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 178418339Butyllithium

Product 1

HCID 86692531HCID 86692531, compoundYield 39.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8058HexaneSolvent

Procedure

To a solution of 2,5-dibromo-3-methylpyridine (3.88 g) in toluene (70 ml) was added dropwise a 1.6 M solution of n-butyllithium in n-hexane (10.6 ml) at −78° C., and stirred at the same temperature for 1 hour. Then, a solution of N-tert-butoxycarbonyl-hexahydroazepin-4-one (3.0 g) in toluene (16 ml) was added dropwise thereto, and stirred at the same temperature for 5 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate) to give 4-(5-bromo-3-methylpyridin-2-yl)-4-hydroxyazepane-1-carboxylic acid tert-butyl ester (2.14 g) as a colorless clear oil.

Workup

  1. stirringstirred at the same temperature for 5 hours
  2. customAfter completion of the reaction
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified with silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d7dd29eb3b5c4036b748f0a09a0b5ef3
Source dataset
uspto-grants-2015_10
Patent number
US09150555B2

Reaction notes

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