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

HRID 1457723Notes

Reaction equation

HRID 1457723 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. Alternatively, 3-cyano-8-methyl-8-azabicyclo[3.2.1]octane (IV) can be prepared by treating tropine (XIII) with thionyl chloride to give 3-chloro-8-methyl-8-azabicyclo[3.2.1]octane (XII) and reacting (XII) with cyanide as described in J. Am. Chem. Soc., (1958) 80, 4677.

Sources & evidence

ORD record
ord-290620ef4d934a20a234c538f2cb7a26
Source dataset
uspto-grants-1998_12
Patent number
US05849754

Reaction notes

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