HCID 67130720, compound → HCID 67130847, compound

HRID 2046795Notes

Reaction equation

HRID 2046795 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-4335b44d66df44fba8e6a8b89d9cb3a2
Source dataset
uspto-grants-2013_11
Patent number
US08592455B2

Reaction notes

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