3-Azetidinol, 1-[[4-(1-methylethyl)phenyl]methyl]- synthesis

Yield:-

Reaction Conditions:

Stage #1: azetidine-3-ol;(4-isopropylbenzaldehyde)with acetic acid in ethanol; for 1 h;
Stage #2: with sodium tris(acetoxy)borohydride in ethnol; for 72 h;
Stage #3: with hydrogenchloride;water in ethanol;

Steps:

2

Preparation 2: l-(4-Isopropylbenzyl)azetidin-3-ol To a solution of azetidin-3-ol (Preparation 1, 6.84 mmol) and 4-isopropylbenzaldehyde (8.21 mmol) in ethanol (45 mL) was added acetic acid (0.5 mL). After stirring for 1 h, sodium triacetoxyborohydride (8.21 mmol) was added, stirring continued for 3 days. Aqueous hydrochloric acid (IM, 30 mL) was added and the mixture concentrated to remove ethanol. The mixture was extracted with diethyl ether (x 2), and the remaining aqueous mixture basified by addition of 2M sodium hydroxide. The solution was then extracted with DCM (x 3). The combined DCM extracts were dried (MgSO₄) and concentrated to afford the title compound; RT = 2.00 min; m/z (ES⁺) = 206.07 [M+H]⁺.

References:

WO2009/50522,2009,A1 Location in patent:Page/Page column 15