Diisopropylamine → 1-(2-Benzyloxy-1-hydroxy-ethyl)-cyclohexanecarbonitrile

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Lithium diisopropylamide was prepared by dropwise addition of n-BuLi (2.03 mL; 2.5 M in Hexanes; 5.08 mmol) to a stirred and cooled (−10° C.) solution of i-Pr2NH (0.84 mL; 6.0 mmol) in dry tetrahydrofuran (40 mL). Stirring was continued for 20 minutes. The mixture was cooled to −78° C. and cyclohexane carbonitrile 1 (500 mg; 4.62 mmol) was added over 5 minutes. After a further 30 minutes, benzyloxyacetaldehyde (0.97 mL; 6.93 mmol) was added dropwise. Stirring was continued at −78° C. for 7 hours. The reaction mixture was then allowed to stir overnight at −20° C. Saturated aqueous NH4Cl was added (10 mL), and the mixture was extracted with diethyl ether (2×20° mL), dried over MgSO4 and evaporated. The residue was purified over silica gel chromatography (ether/heptane 1:1) to give 2 as a white solid (872 mg; 3.37 mmol; 73%)

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