Diazomethane → HCID 71008072, compound

HRID 2361712Notes

Reaction equation

HRID 2361712 reaction equation
[N+](=[CH2:3])=[N-].[O:4]=[C:5]1[CH:12]2[CH2:13][C:8]3([NH:15][C:16](=[O:18])[CH3:17])[CH2:9][CH:10]([CH2:14][CH:6]1[CH2:7]3)[CH2:11]2.[OH-].[K+]>CO.O>[O:4]=[C:5]1[CH2:3][CH:12]2[CH2:13][C:8]3([NH:15][C:16](=[O:18])[CH3:17])[CH2:9][CH:10]([CH2:14][CH:6]1[CH2:7]3)[CH2:11]2

Participants

6

Reactant 3

HCID 9550DiazomethaneHCID 14797Potassium HydroxideHCID 5338964N-(4-oxo-1-adamantyl)acetamide

Product 1

HCID 71008072HCID 71008072, compoundYield 90.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

A solution of diazomethane (Diazald, 2.70 g) in MeOH (15 mL) was added dropwise to a mixture of ketone 1A (997 mg) and KOH (3.81 g) in MeOH (10 mL) and water (1.8 mL) at 0° C. over a period of 1.5 h. The reaction mixture was allowed to warm to rt and was maintained for 16 h. The resulting suspension was concentrated and was diluted with water (50 mL). The resulting aqueous suspension was extracted with ether (1×), then with DCM (2×), and the combined organic layers were dried (Na2SO4) and concentrated. The residue was purified by silica gel chromatography (0/100 to 10/90 MeOH/EtOAc) to provide 964 mg of ketone 8A as a white solid. Data: LC/MS (ESR) m/z 222 [M+1]+, 244 [M+Na]+.

Workup

  1. temperaturewas maintained for 16 h
  2. concentrationThe resulting suspension was concentrated
  3. additionwas diluted with water (50 mL)
  4. extractionThe resulting aqueous suspension was extracted with ether (1×)
  5. dry with materialwith DCM (2×), and the combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0/100 to 10/90 MeOH/EtOAc)

Sources & evidence

ORD record
ord-35de7e674d944118bcbadceb93808acc
Source dataset
uspto-grants-2014_04
Patent number
US08691808B2

Reaction notes

Loading…