HCID 67130720, compound → HCID 67134452, compound

HRID 2192568Notes

Reaction equation

HRID 2192568 reaction equation
[Si:1]([O:8][CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][C:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-])=O)=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]>CO.[Pd]>[Si:1]([O:8][CH:9]1[CH2:14][CH:13]([CH3:15])[CH2:12][CH:11]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH2:22])[CH2:10]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 67130720HCID 67130720, compound

Product 1

HCID 67134452HCID 67134452, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)-3-nitropyridine (1.0 equiv.) in methanol, at a concentration of 0.1 M, was added 10% palladium on carbon (0.1 eq.). The resultant heterogeneous solution was put under an atmosphere of hydrogen and was stirred for 15 hours. At this time the mixture was filtered through a pad of celite eluting with methanol. The volatiles were removed in vacuo yielding 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohexyl)pyridin-3-amine (90%). LCMS (m/z): 321.3 (MH+); LC Rt=3.85 min.

Workup

  1. filtrationAt this time the mixture was filtered through a pad of celite
  2. washeluting with methanol
  3. customThe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-ca009750b6ae474481c5a76f0c8cc149
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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