Ethanol → (4R,5R)-1-azabicyclo[3.3.1]nonane-4-carbonitrile

HRID 356107Notes

Reaction equation

[N:1]12[CH2:9][CH:5]([CH2:6][CH2:7][CH2:8]1)[C:4](=O)[CH2:3][CH2:2]2.C1(C)C=CC(S([CH2:20][N+:21]#[C-])(=O)=O)=CC=1.C(O)C.CC(C)([O-])C.[K+]>C(COC)OC>[N:1]12[CH2:9][C@H:5]([CH2:6][CH2:7][CH2:8]1)[C@H:4]([C:20]#[N:21])[CH2:3][CH2:2]2

Participants

Conditions

Temperature: 5 °C

Procedure

To a solution of 2.00 g of 1-azabicyclo[3.3.1]nonan-4-one in 100 ml of dimethoxyethane, 3.65 g of p-toluenesulfonylmethylisocyanide and 1.13 g of ethanol were added, followed by cooling to 5° C. Then, 4.00 g of potassium tert-butoxide was added while keeping the internal temperature below 10° C. The mixture was stirred at room temperature for 30 minutes, followed by further stirring at 40° C. for 30 minutes. The precipitate thus formed was removed by filtration. The residue obtained by evaporation of the solvent was purified by an alumina column chromatography (eluent: chloroform:hexane=1:1). The resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1), whereby 1.01 g of (4R*,5R*)-1-azabicyclo[3.3.1]nonane-4-carbonitrile was obtained.

Workup

customthe internal temperature below 10° C
stirringby further stirring at 40° C. for 30 minutes
customThe precipitate thus formed
customwas removed by filtration
customThe residue obtained by evaporation of the solvent
customwas purified by an alumina column chromatography (eluent: chloroform:hexane=1:1)
customThe resulting crude product was then purified by silica gel column chromatography (eluent: chloroform:methanol=20:1)

Sources & evidence

ORD record: ord-2e57fe313bf04f39bdf3ad8a3c083277
Source dataset: uspto-grants-1998_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05834499

Reaction notes

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