[5-(2-Fluoro-5-nitro-phenyl)-5-trifluoromethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl]-carbamic acid tert-butyl ester → HCID 66665843, compound

HRID 221767Notes

Reaction equation

HRID 221767 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH2:9][O:10][CH2:11][CH2:12][C:13]([C:19]2[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:20]=2[F:28])([C:15]([F:18])([F:17])[F:16])[N:14]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.C1COCC1.[Pd]>[C:1]([O:5][C:6](=[O:29])[NH:7][C:8]1[CH2:9][O:10][CH2:11][CH2:12][C:13]([C:19]2[CH:24]=[C:23]([NH2:25])[CH:22]=[CH:21][C:20]=2[F:28])([C:15]([F:17])([F:16])[F:18])[N:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 66666190[5-(2-Fluoro-5-nitro-phenyl)-5-trifluoromethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl]-carbamic acid tert-butyl ester

Product 1

HCID 66665843HCID 66665843, compoundYield 87.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of [5-(2-fluoro-5-nitro-phenyl)-5-trifluoromethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl]-carbamic acid tert-butyl ester (1.69 g, 4.01 mmol) in 10 mL ethanol and 10 mL THF was brought under nitrogen atmosphere and 500 mg of 5% Pd on charcoal was added. The reaction mixture was then stirred under a hydrogen atmosphere (balloon) for 6 hours. Then it was filtered over celite and evaporated. The crude product was crystallized from hexane/TBME to give 1.38 g of the title compound as white crystals.

Workup

  1. filtrationThen it was filtered over celite
  2. customevaporated
  3. customThe crude product was crystallized from hexane/TBME

Sources & evidence

ORD record
ord-f5f2053c2bdb4fa6b0c24edd0c79556d
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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