3,3-DIMETHYL-4-PHENYL-2-AZETIDINONE synthesis

10synthesis methods

Product Name:3,3-DIMETHYL-4-PHENYL-2-AZETIDINONE
CAS Number:7486-93-3
Molecular formula:C11H13NO
Molecular Weight:175.23

DIMETHYLKETENE METHYL TRIMETHYLSILYL ACETAL

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[1-PHENYL-METHYLIDENE]-TRIMETHYLSILANYL-AMINE

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Yield:7486-93-3 212 mg

Reaction Conditions:

Stage #1: 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene;N-benzylidene-1,1,1-trimethylsilanamine in tetrahydrofuran at 85; for 1.5 h;
Stage #2: with ammonium chloride in tetrahydrofuran;

Steps:

Representative Procedure for the synthesis of b-Lactams

General procedure: To a solution of aryl aldehyde (2.0 mmol) in anhydrous tetrahydrofuran (2 mL) at 0^oC, was added a 1.0 M solution of lithium bis(trimethylsilyl)amide (2 mL) in tetrahydrofuran and the resulting solution was stirred at ambient temperature for 30 min. After this time, 1-methoxy-2-methyl-1-(trimethylsilyloxy)propene (0.61 mL, 3.0 mmol; 1.5 equiv) was added and the reaction mixture was heated with stirring at 80^oC (oil-bath temperature, reflux) for 1.5 h. TLC at this point, indicated complete conversion of starting aryl aldehyde to a significantly more polar spot (70/30, hexanes/ethyl acetate mixture). The reaction was quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate (3x20 mL). The combined organic layer was washed with brine, dried, and concentrated to provide a crude solid (remarkably clean by ¹H NMR) which was recrystallized exhibiting mp and yield shown in Table 1 3,3-Dimethyl-4-phenyl-azetidin-2-one (2a) Prepared according to the representative procedure, reported in the communication, utilizing benzaldehyde (2 mmol, 212 mg, 85% yield). An analytically pure sample (298 mg, 85% yield) obtained by recrystallization, (hexanes/dichloromethane or hexanes/ethyl acetate) exhibited the following data: mp 104-105^oC. ¹H NMR (400 MHz, CDCl₃): d 7.41-7.25 (m, 5H), 6.13 (bs, 1H), 4.52 (s, 1H), 1.48 (s, 3H), 0.79 (s, 3H). ¹³C NMR (100 MHz, CDCl₃): d 174.87, 137.80, 128.51, 127.82, 126.03, 63.23, 57.00, 22.54, 18.15.

References:

Panagiotou, Maria;Demos, Vasileios;Magriotis, Plato Α. [Tetrahedron Letters,2020,vol. 61,# 40,art. no. 152375] Location in patent:supporting information

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999-97-3 Synthesis