HCID 67426414, compound → 1231930-19-0

HRID 2264355Notes

Reaction equation

HRID 2264355 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[N:17][C:18]([N+:21]([O-])=O)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd].O1CCCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[N:17][C:18]([NH2:21])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67426414HCID 67426414, compound

Product 1

HCID 674264061231930-19-0Yield 97.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add palladium over carbon 10% (0.6 g) to a suspension of 4-(6-nitro-pyridin-3-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (5.65 g) in a mixture tetrahydrofuran (THF)/methanol (30/30 mL/mL). Hydrogenate in a Parr apparatus at 2 atm overnight. Filter through a celite pad, wash with DCM and methanol. Purify by silica gel column chromatography eluting with DCM/methanol (10%)/ammonia (1%) to afford 5 g of the title compound. MS (ES+): m/z=294 (M+H)+.

Workup

  1. customat 2 atm overnight
  2. filtrationFilter through a celite pad
  3. washwash with DCM and methanol
  4. customPurify by silica gel column chromatography
  5. washeluting with DCM/methanol (10%)/ammonia (1%)

Sources & evidence

ORD record
ord-0a97c40c1a134722b51d17921741bb7c
Source dataset
uspto-grants-2010_12
Patent number
US07855211B2

Reaction notes

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