1-hydroxycyclohexane-1-carbonitrile

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of cyclohexanone cyanohydrin (2 g, 15.98 mmol) in anhydrous THF (40 mL) at rt was added portion-wise LiAlH4 (1.82 g, 47.94 mmol). The reaction vessel was sealed and the mixture was heated at 80° C. for 5 h. The mixture was cooled to 0° C. and water (1 mL), 1M aq NaOH (1 mL), and water (3 mL) were added sequentially. To the resulting mixture was added DCM and saturated aq sodium potassium tartrate, and the mixture stirred for 3 h. The organic layer was separated and further washed with brine. The organic layer was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to afford 1-(aminomethyl)cyclohexanol (1.3 g) which was not purified further. LCMS (ESI) m/z 130 (M+H)+. The reaction vessel was sealed The mixture was cooled to 0° C. The organic layer was separated further washed with brine The organic layer was separated dried over MgSO4 filtered concentrated under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a similar manner, 1-aminoisobutyronitrile was prepared by substituting for cyclohexanone cyanohydrin an equivalent amount of acetone cyanohydrin.

Conditions: temp:10.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Sodium carbonate (30.0 g., 0.283 mole) was dissolved in 200.2 g. of water, the system was closed and anhydrous liquid HCN (3.46 g., 0.128 mole) was added to the solution. Little, if any, heat was given off in the reaction and the product solution was clear. Cyclohexanone (32.05 g., 0.327 mole) was injected into the system with good mixing. The mixture heated up immediately 10°C. The organic and aqueous phases were mixed for 15 minutes longer and then allowed to separate. The organic layer (35.9 g.) was analyzed for free HCN, showing none, followed by an analysis for both combined and free HCN which showed 3.19 g. (0.118 mole) or 92% of the original HCN injected appearing in the organic phase as cyanohydrin. Little, if any, heat was given off in the reaction The organic and aqueous phases were mixed for 15 minutes longer to separate