HCID 58386784, compound → HCID 58386794, compound

HRID 924449Notes

Reaction equation

HRID 924449 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:5][C@@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:3]1.[H][H]>CO.[Pd]>[NH2:14][C:9]1[CH:10]=[N:11][CH:12]=[CH:13][C:8]=1[N:6]1[CH2:7][C@H:2]([CH3:1])[CH2:3][C@H:4]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:5]1

Participants

5

Reactant 2

HCID 58386784HCID 58386784, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58386794HCID 58386794, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of tert-butyl [(3S,5R)-5-methyl-1-(3-nitropyridin-4-yl)piperidin-3-yl]carbamate (1.14 g, 3.39 mmol) in MeOH was hydrogenated in the presence of 10% Pd on carbon (0.14 g) under 45 psi of hydrogen overnight. The mixture was filtered through diatomaceous earth. The filtrate was concentrated under reduced pressure to give the sub-title compound (1.04 g, 100%). LCMS calc. for C16H27N4O2 (M+H)+: m/z=307.2. found: 307.3.

Workup

  1. filtrationThe mixture was filtered through diatomaceous earth
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-95d82f3c10ce4b1ba3ee208d91f5eaec
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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