Diethyl Ether → HCID 19097374, compound

HRID 2255418Notes

Reaction equation

HRID 2255418 reaction equation
[CH3:1]I.[Mg].[CH3:4][CH:5]1[C:10]2([CH3:14])[CH:11]([CH3:13])[CH2:12][CH:7]([CH:8](C(OCC)=O)[CH2:9]2)[N:6]1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[NH4+].[Cl-].CC[O:31][CH2:32][CH3:33]>>[CH3:1][C:32]([CH3:33])([CH:8]1[CH:7]2[CH2:12][CH:11]([CH3:13])[C:10]([CH3:14])([CH:5]([CH3:4])[N:6]2[CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:9]1)[OH:31]

Participants

6

Reactant 5

HCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 19097377HCID 19097377, compound

Product 1

HCID 19097374HCID 19097374, compoundYield 98%

Procedure

Methyl iodide (138.4 g, 0.98 mole) was added dropwise over 1.5 hours to magnesium turnings (23 7 g, 0.98 mole) in ether (300 mL). The solution was diluted to a total volume of 1 liter and was stirred at room temperature for 2 hours. The solution was filtered through a glass wool plug into a second flask under nitrogen and a solution of ethyl 3,4,8-trimethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]-octane-6-carboxylate (87.9 g, 0.28 mole) in ether (400 mL) was added over 2 hours. The mixture was stirred at room temperature for 1 hour, poured into a mixture of saturated NH4Cl (700 mL) and ice-water (1000 mL) and the organic layer was separated. The aqueous phase was extracted with ether (2×700 mL) and the combined organic layers were washed with water (2×500 mL), then brine (500 mL) and were dried over anhydrous MgSO4. The solvent was removed in vacuo to afford 82.5 g (98%) α,α,3,4,8-pentamethyl-2-(phenylmethyl)-2-azabicyclo[2.2.2]octane-6-methanol. A small portion of the product (5.0 g) was treated with ethereal HCl to afford the hydrochloride salt as a white solid, m.p. 221°-222° C. (dec) when recrystallized from ethanol/ether.

Workup

  1. additionThe solution was diluted to a total volume of 1 liter
  2. filtrationThe solution was filtered through a glass wool plug into a second flask under nitrogen
  3. stirringThe mixture was stirred at room temperature for 1 hour
  4. customthe organic layer was separated
  5. extractionThe aqueous phase was extracted with ether (2×700 mL)
  6. washthe combined organic layers were washed with water (2×500 mL)
  7. dry with materialbrine (500 mL) and were dried over anhydrous MgSO4
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d2d0e25f70214cb689437b88c3115feb
Source dataset
uspto-grants-1993_08
Patent number
US05240935

Reaction notes

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