Methanol → HCID 59226410, compound

HRID 73578Notes

Reaction equation

HRID 73578 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-7bd5f804ffe54a1fb494708eab7a00a2
Source dataset
uspto-grants-2014_09
Patent number
US08829193B2

Reaction notes

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