Methanol → HCID 59226410, compound

HRID 1920216Notes

Reaction equation

HRID 1920216 reaction equation
[Si:1]([O:8][CH:9]1[CH:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=[C:12]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][C:24]=2[N+:29]([O-])=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CO>CC(O)=O.[Fe]>[NH2:29][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][C:23]=1[C:12]1[CH2:11][CH2:10][CH:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2])[CH:14]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH:13]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 59226562HCID 59226562, compound

Product 1

HCID 59226410HCID 59226410, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of (+/−)-tert-butyl 6-(tert-butyldimethylsilyloxy)-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.) in AcOH (0.18 M) was added Fe (6.0 equiv.) and the reaction was stirred for 20 h. Worked up by diluting the reaction with methanol, filtered, and concentrated the filtrate. To the crude was added ethyl acetate and saturated NaHCO3, the organics were dried with sodium sulfate and concentrated to give (+/−)-tert-butyl 3-(3-aminopyridin-4-yl)-6-(tert-butyldimethylsilyloxy)cyclohex-2-enylcarbamate as a yellow oil in 94% yield. LCMS (m/z): 420.3 (MH+), LC Rt=3.88 min.

Workup

  1. additionby diluting
  2. filtrationfiltered
  3. concentrationconcentrated the filtrate
  4. additionTo the crude was added ethyl acetate and saturated NaHCO3
  5. dry with materialthe organics were dried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ce3581ca820744609a10cf7a1a8c0817
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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