(S)-tert-butyl methyl(1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-yl)carbamate → (S)-tert-butyl 1-(2-amino-4-(trifluoromethyl)phenyl)piperidin-3-yl(methyl)carbamate

HRID 1042648Notes

Reaction equation

HRID 1042648 reaction equation
[CH3:1][N:2]([C@H:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][C:17]=2[N+:26]([O-])=O)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6]>[Pd].CO>[NH2:26][C:17]1[CH:18]=[C:19]([C:22]([F:25])([F:23])[F:24])[CH:20]=[CH:21][C:16]=1[N:12]1[CH2:13][CH2:14][CH2:15][C@H:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:6])([CH3:7])[CH3:8])[CH2:11]1

Participants

4

Reactant 1

HCID 16109042(S)-tert-butyl methyl(1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-yl)carbamate

Product 1

HCID 16109045(S)-tert-butyl 1-(2-amino-4-(trifluoromethyl)phenyl)piperidin-3-yl(methyl)carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 100 mL RBF was added (S)-tert-butyl methyl(1-(2-nitro-4-(trifluoromethyl)phenyl)piperidin-3-yl)carbamate (1.75 g, 4.34 mmol) and palladium, 10 wt. % on activated carbon wet (0.923 g, 0.868 mmol) under nitrogen. MeOH was added via syringe, and the atmosphere was purged with hydrogen from a balloon. The reaction was allowed to stir rapidly under hydrogen for 8 h. The flask was purged with nitrogen, filtered through celite, rinsing with 100 mL MeOH, and concentrated to give (S)-tert-butyl 1-(2-amino-4-(trifluoromethyl)phenyl)piperidin-3-yl(methyl)carbamate as a gray solid. MS m/z=374 [M+H]+. Calc'd for C18H26F3N3O2: 373.

Workup

  1. customthe atmosphere was purged with hydrogen from a balloon
  2. customThe flask was purged with nitrogen
  3. filtrationfiltered through celite
  4. washrinsing with 100 mL MeOH
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-85b24de19b0048a890810b1af9bb04ac
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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