Tetrahydrofuran → HCID 58495157, compound

HRID 516233Notes

Reaction equation

HRID 516233 reaction equation
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[C:23]([N+:24]([O-])=O)=[CH:22][C:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14][C:8]=2[C:7]=1[CH3:27].C1COCC1>CCO.[Pd]>[CH3:27][C:7]1[C:8]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:21])[CH3:19])=[O:16])[CH2:11][CH2:10][C:9]=2[CH:22]=[C:23]2[NH:24][C:3](=[O:2])[CH2:4][O:5][C:6]=12

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58495281HCID 58495281, compound

Product 1

HCID 58495157HCID 58495157, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of 967 mg of t-butyl 7-(2-methoxy-2-oxoethoxy)-6-methyl-8-nitro-1,2,4,5-tetrahydro-3H-3-benzazepine-3-carboxylate in 25 ml of EtOH was added 97 mg of 10% palladium on carbon under an argon atmosphere, followed by stirring for 2 hours at normal pressure under a hydrogen atmosphere. To the reaction mixture was added 200 ml of THF, then the catalyst was removed using celite, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc) to obtain 629 mg of t-butyl 11-methyl-3-oxo-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate as a white solid.

Workup

  1. customthe catalyst was removed
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)

Sources & evidence

ORD record
ord-7e87cb2a0b9c4d49b23e92ecd2547d4d
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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