Sodium Hydroxide → 2-(1-Aminoindan-5-yl)-2-methylpropionitrile

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Reaction Steps

2-Methyl-2-(1-oxoindan-5-yl)-propionitrile (6.00 g, 30.1 mmol) was added to a mixture of ammonium acetate (69.6 g, 903 mmol) in IPA (600 mL) under nitrogen atmosphere at ambient temperature. After stirring 1 hour, sodium cyanoborohydride (6.62 g, 105 mmol) was added to the mixture and refluxed for 2 hours. The reaction solution was cooled to room temperature, added 3N sodium hydroxide (300 mL), extracted with TBME (2×500 mL) and concentrated the organic extracts to an oil. Dissolved in ethyl acetate (500 mL), extracted with 1N hydrochloric acid (3×300 mL), combined the aqueous layers, added 3N sodium hydroxide (400 mL), extracted with ethyl acetate (2×1 L), dried with brine and anhydrous sodium sulfate, and concentrated. Obtained 2-(1-aminoindan-5-yl)-2-methylpropionitrile (4.26 g, 71%) as a yellow oil. MS (DCI/NH3) m/z: 201.10 [M+H]+. 1H NMR (DMSO-d6) δ: 1.60 (m, 1H), 1.66 (s, 6H), 1.93 (br, 2H), 2.35 (m, 1H), 2.74 (m, 1H), 2.86 (m, 1H), 4.17 (t, 1H), 7.32 (m, 3H).

Provenance & Evidence