8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → 3-Chloro-8-methyl-8-azabicyclo(3.2.1)octane

HRID 1936723Notes

Reaction equation

HRID 1936723 reaction equation
C([CH:3]1[CH2:9][CH:8]2[N:10]([CH3:11])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1)#N.CN1C2CC(CC1CC2)=O.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[O-]CC.[K+].CN1C2CC(O)CC1CC2.S(Cl)([Cl:51])=O>>[Cl:51][CH:3]1[CH2:9][CH:8]2[N:10]([CH3:11])[CH:5]([CH2:6][CH2:7]2)[CH2:4]1

Participants

7

Reactant 6

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 24386Thionyl ChlorideHCID 79038Npc164516HCID 161915Tosylmethyl isocyanideHCID 5576238-Methyl-8-azabicyclo[3.2.1]octane-3-carbonitrile2×HCID 23670592Potassium ethoxide

Product 1

HCID 1375273-Chloro-8-methyl-8-azabicyclo(3.2.1)octane

Procedure

3-Cyano-8-methyl-8-azabicyclo[3.2.1]octane (IV) can be prepared by treating tropinone (V) with tosylmethyl isocyanide in the presence of a suitable base, such as potassium ethoxide. As an alternative 3-cyano-8-methyl-8-azabicyclo[3.2.1]octane (IV) can be prepared from tropine (XII) by treatment with thionyl chloride to give alternative 3-chloro-8-methyl-8-azabicyclo[3.2.1]octane (XIII) followed by treatment with cyanide as described in J. Am. Chem. Soc., 1958 80, 4677.

Sources & evidence

ORD record
ord-f3a5f329e7d3445a9a670b6a22e8caa4
Source dataset
uspto-grants-2002_05
Patent number
US06391883B1

Reaction notes

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