Compound 102
(S)-5-(4-(azetidin-1-yl)benzyl)-2,2,3-trimethylimidazolidin-4-one
From: Practical and regioselective amination of arenes using alkyl amines
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Compound data: NMR
Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
Following GP2 outlined for compound 45, in 1,1,1,3,3,3-hexafluoro-i-propanol (HFIP) at 0 °C, but using 1.0 equiv of (S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one, 1.5 equiv. of azetidine hydrochloride 1.5 equiv.of NCS, 1.6 of equiv of N,N-diisopropylehtylamine and 8.0 equiv. of HClO4, (S)-5-benzyl-2,2,3-trimethylimidazolidin-4-one (26 mg, 0.1 mmol) gave 102 and 102’ (16 mg, 49%) as a wax. 102:102’ = 2:1. Rf 0.21 [CHCl3–MeOH (98:2)]; FT-IR νmax (film)/cm–1 3023, 2876, 1723, 1702, 1578, 1181, 1012; 1H NMR (CDCl3, 500 MHz) δ 7.05 (2H, d, J = 7.9 Hz), 6.39 (2H, d, J = 7.9 Hz), 3.84 (4H, t, J = 7.1 Hz), 3.73 (1H, t, J = 5.0 Hz), 3.00 (2H, t, J = 5.1 Hz), 2.74 (3H, s), 2.34 (2H, p, J = 7.1 Hz), 1.44 (1H, d, J = 5.1 Hz), 1.25 (3H, s), 1.14 (3H, s); 13C NMR (126 MHz, CDCl3) δ 173.7, 150.9, 130.2, 125.3, 111.8, 75.7, 59.5, 52.7, 36.1, 27.2, 25.5, 25.4, 17.1; HRMS (ASAP POS): Found MH+ 274.1918, C16H24N3O requires 274.1914.
