Isobutylamine → HCID 86617383, compound

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Reaction Steps

Sodium triacetoxyborohydride (2.9 g, 14 mmol, 1.4 eq) is added to a solution of isobutylamine (0.77 g, 10 mmol, 1.05 eq) and N-(tert-butoxycarbonyl)-L-prolinal (2 g, 10 mmol, 1 eq) in 1,2-dichloroethane (35 ml). After 1 hr water (25 ml) followed by 2N aqueous sodium hydroxide (25 ml) is added. The aqueous layer is separated and extracted with dichloromethane (3×50 ml). The organic layers are combined and dried over magnesium sulphate, filtered, and concentrated in vacuo giving a residue. The residue is purified by flash chromatography, eluting with 20-70% methanol in ethyl acetate to give the tert-butyl (2S)-2-[(isobutylamino)methyl]pyrrolidine-1-carboxylate (1.95 g, 76%): 1H NMR (300 MHz, CDCl3) δH: 3.69-4.07 (1H, m), 3.19-3.50 (2H, m), 2.67-2.87 (1H, m), 2.48-2.65 (1H, m), 2.35-2.47 (2H, m), 1.62-2.01 (5H, m), 1.34-1.53 (9H, m) and 0.88 (6H, d); LCMS: Rt=2.74 (6 min method) [M+H]=257.5.

Provenance & Evidence