Formamide → HCID 86691658, compound

HRID 2406872Notes

Reaction equation

HRID 2406872 reaction equation
[CH3:1][C@:2]12[C:11]([CH3:13])([CH3:12])[C@H:8]([CH2:9][CH2:10]1)[C:4]1([CH2:7][CH2:6][CH2:5]1)[C:3]2=O.[CH:15]([NH2:17])=[O:16]>C(O)=O>[CH3:1][C:2]12[C:11]([CH3:13])([CH3:12])[CH:8]([CH2:9][CH2:10]1)[C:4]1([CH2:7][CH2:6][CH2:5]1)[CH:3]2[NH:17][CH:15]=[O:16]

Participants

4

Reactant 2

HCID 713FormamideHCID 67126910HCID 67126910, compound

Product 1

HCID 86691658HCID 86691658, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of (1S,4R)-4,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,1′-cyclobutan]-3-one (1.60 g, 8.32 mmol) and formamide (10 mL) in formic acid (7 mL) was stirred at 175° C. for 72 h. The reaction mixture was cooled to ambient temperature, poured into 200 mL of ice-water, and extracted with ether (2×50 mL). The combined ether extracts were washed with water (40 mL), dried over anhydrous sodium sulfate and concentrated to obtain N-(4,7,7-trimethylspiro[bicyclo[2.2.1]heptane-2,1′-cyclobutan]-3-yl)formamide (1.55 g, 84.2% yield) as gum.

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. extractionextracted with ether (2×50 mL)
  3. washThe combined ether extracts were washed with water (40 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-eb297aa581234d26b58a6ff18f47132a
Source dataset
uspto-grants-2014_08
Patent number
US08809397B2

Reaction notes

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