Tert-butyl 4-(2-(difluoromethoxy)-4-nitrophenoxy)piperidine-1-carboxylate → Tert-butyl 4-(4-amino-2-(difluoromethoxy)phenoxy)piperidine-1-carboxylate

HRID 633431Notes

Reaction equation

HRID 633431 reaction equation
[F:1][CH:2]([F:27])[O:3][C:4]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][C:5]=1[O:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1>[Pd].CO>[NH2:24][C:22]1[CH:21]=[CH:20][C:5]([O:6][CH:7]2[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[CH2:9][CH2:8]2)=[C:4]([O:3][CH:2]([F:27])[F:1])[CH:23]=1

Participants

4

Reactant 1

HCID 86704525Tert-butyl 4-(2-(difluoromethoxy)-4-nitrophenoxy)piperidine-1-carboxylate

Product 1

HCID 86704526Tert-butyl 4-(4-amino-2-(difluoromethoxy)phenoxy)piperidine-1-carboxylateYield 63.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The general hydrogenation procedure as described herein was used with tert-butyl 4-(2-(difluoromethoxy)-4-nitrophenoxy)piperidine-1-carboxylate (193 mg, 0.5 mmol), palladium on charcoal (39 mg) and MeOH (5 mL) under atmospheric pressure (H2 balloon) to give the product (113 mg, 63% yield) after purification by column chromatography on silica gel using EtOAc/heptane (2:8 to 6:4) as eluent.

Sources & evidence

ORD record
ord-3d8b908a75a7409495981f94d1a99f33
Source dataset
uspto-grants-2016_04
Patent number
US09321763B2

Reaction notes

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