HCID 58993582, compound → HCID 58993480, compound

HRID 391381Notes

Reaction equation

HRID 391381 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:7][O:8][CH2:9][C:10]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:29]=[C:30]([C:32]([F:35])([F:33])[F:34])[CH:31]=1)[CH2:7][O:8][CH2:9][C:10]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][CH2:11]1

Participants

4

Reactant 1

HCID 58993582HCID 58993582, compound

Product 1

HCID 58993480HCID 58993480, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

tert-Butyl 4-((3-nitro-5-(trifluoromethyl)benzyloxy)methyl)-4-phenylpiperidine-1-carboxylate (118 mg, 0.24 mmol) in methanol (2.5 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 12 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated to afford 90 mg (80%). LC/MS (HPLC method 3): tR=3.10 min, 465.22 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customto afford 90 mg (80%)

Sources & evidence

ORD record
ord-ebe11a0b7c6f40d599f650616856f68f
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Reaction notes

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