HCID 67130720, compound → HCID 67130847, compound

HRID 2192567Notes

Reaction equation

HRID 2192567 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]>C(O)(=O)C.[Fe]>[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[NH2:22])=[CH: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 67130847HCID 67130847, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A heterogeneous solution of 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)-3-nitropyridine (1.0 eq.) and iron (6.0 eq) in acetic acid, at a concentration of 0.4 M, was stirred vigorously for 2 hours. The mixture was then passed through a celite pad, eluting with MeOH. Upon removal of the volatiles in vacuo, the residue was dissolved in EtOAc, washed with Na2CO3(sat.), NaCl(sat.), was dried over MgSO4, was filtered and the volatiles were removed in vacuo yielding 4-(3-(tert-butyldimethylsilyloxy)-5-methylcyclohex-1-enyl)pyridin-3-amine (78%). LCMS (m/z): 319.3 (MH+); LC Rt=3.77 min.

Workup

  1. washeluting with MeOH
  2. customUpon removal of the volatiles in vacuo
  3. dissolutionthe residue was dissolved in EtOAc
  4. washwashed with Na2CO3(sat.), NaCl(sat.)
  5. dry with materialwas dried over MgSO4
  6. filtrationwas filtered
  7. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-f8ece10790554a53b092695d2f0785d5
Source dataset
uspto-grants-2012_12
Patent number
US08329732B2

Reaction notes

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