Water → HCID 11421978, compound

Participants

Reaction Steps

(R,R)-1,2-bis(3,5-di-tert-butylsalicylidenamino)cyclohexane (5.0 g, 9.2 mmol, 1 mol equiv) is suspended in a mixture of dichloromethane/96% ethanol (1:3, 200 ml). Then NaBH4 (1.74 g, 45.7 mmol, 5 mol equiv) is added portionwise and the mixture is stirred until it becomes colorless (24 h). Water (50 ml) is added to the reaction mixture and it is extracted with dichloromethane (3×50 ml). The combined organic layers are dried over Na2SO4 and the solvent is evaporated to give the title product as a solid residue (4.95 g, 98% yield): 1H NMR (300 MHz, CDCl3) δ 7.30 (1H, d), 6.96 (1H, d), 4.13 (1H, d), 3.99 (1H, d), 2.56 (1H, m), 2.26 (1H, m), 1.78 (1H, m), 1.47 (9H, s), 1.37 (11H, s); 13C NMR (75 MHz, CDCl3) δ 24.1, 29.6, 30.7, 31.7, 34.1, 34.8, 50.8, 59.8, 122.3, 123.0, 123.1, 135.9, 140.6, 154.3; ESI mass spectrum: 551 [M+H]+.

Provenance & Evidence