Trimethylsilyl cyanide → HCID 15176140, compound

HRID 2165532Notes

Reaction equation

C[Si]([C:5]#[N:6])(C)C.[N:7]12[CH2:15][CH:11]([CH2:12][CH2:13][CH2:14]1)[C:10](=[O:16])[CH2:9][CH2:8]2>ClCCl.[I-].[Zn+2].[I-]>[NH2:6][CH2:5][C:10]1([OH:16])[CH:11]2[CH2:15][N:7]([CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

Trimethylsilyl cyanide (3 ml) was added dropwise to a stirred solution of 1-azabicyclo[3.3.1]nonan-4-one (2.5 g) and zinc iodide (0.15 g) in dry dichloromethane (20 ml) and the resulting mixture was heated at reflux for 4 hours. The mixture was cooled and the solvent removed at reduced pressure; the residue was dissolved in dry tetrahydrofuran (20 ml) and cooled to 0° C. A solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added and the resulting solution stirred overnight at room temperature. Water (0.7 ml), followed by 15% sodium hydroxide (aq) (0.7 ml) and water (2.1 ml) were then added and the precipitate removed by filtration. Evaporation of the filtrate yielded the title compound (2.2 g); δH (360 MHz, CDCl3) 1.2-1.3 (2H, m, CH2), 1.34 (1H, m, CHH), 1.41 (1H, m, CHH), 1.6 (2H, m, CH2), 1.7-1.74 (1H, m, CHH), 1.76-1.91 (2H, m, CH2), 2.11-2.16 (1H, m, CHH), 2.67-3.18 (8H, m); m/z 170 (M+).

Workup

temperaturethe resulting mixture was heated
temperatureat reflux for 4 hours
temperatureThe mixture was cooled
customthe solvent removed at reduced pressure
dissolutionthe residue was dissolved in dry tetrahydrofuran (20 ml)
additionA solution of lithium aluminium hydride in tetrahydrofuran (18 ml of 1.0M soln) was then added
additionwere then added
customthe precipitate removed by filtration
customEvaporation of the filtrate

Sources & evidence

ORD record: ord-3216517382fb49deaa2acd4da1c4f945
Source dataset: uspto-grants-1990_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04940703

Reaction notes

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