Thionyl Chloride → Methyl 1-azabicyclo[2.2.2]oct-2-ene-3-carboxylate--hydrogen chloride (1/1)

HRID 1248653Notes

Reaction equation

HRID 1248653 reaction equation
O[C:2]1([C:10]([O:12][CH3:13])=[O:11])[CH:7]2[CH2:8][CH2:9][N:4]([CH2:5][CH2:6]2)[CH2:3]1.S(Cl)([Cl:16])=O>>[ClH:16].[CH3:13][O:12][C:10]([C:2]1[CH:7]2[CH2:6][CH2:5][N:4]([CH2:9][CH2:8]2)[CH:3]=1)=[O:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2824485Methyl 3-hydroxy-1-azabicyclo[2.2.2]octane-3-carboxylate

Product 1

HCID 23053204Methyl 1-azabicyclo[2.2.2]oct-2-ene-3-carboxylate--hydrogen chloride (1/1)

Procedure

Powdered 3-hydroxy-3-methoxycarbonyl-1-azabicyclo[2.2.2]octane (16.0 g, 0.086 mol) was added protionwise to thionyl chloride (100 ml) at 0°. Following the addition, the reaction mixture was stirred and heated under reflux for 48 h. The thionyl chloride was then removed under reduced pressure to afford a solid, which was recrystallised from acetone, giving 3-methoxycarbonyl-1-azabicyclo[2.2.2]oct-2-ene hydrochloride, m.p. 178°-179°.

Workup

  1. additionthe addition
  2. temperatureheated
  3. temperatureunder reflux for 48 h
  4. customThe thionyl chloride was then removed under reduced pressure
  5. customto afford a solid, which
  6. customwas recrystallised from acetone

Sources & evidence

ORD record
ord-f6e7dace48c14704b27d917a1ea5c57e
Source dataset
uspto-grants-1985_06
Patent number
US04525475

Reaction notes

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