3-Phthalimidopropionaldehyde

5L reaction flask was charged 1.5L of ethyl acetate, the raw material phthalimide (441.4g, 3.0mol, 1.0eq), stirred mechanically, then added acrolein feed (240.6mL, 3.6mol, 1.2eq), 30 within minutes the system was heated to 65 , MeOH was added 40wt.percent BnNMe3OH of (2.0mL, 0.0015eq.), the reaction system at 65-70 25 min, then MeOH was added 40wt.percent BnNMe3OH of (2.0mL, 0.0015 . eq), followed by reaction for 35 minutes 65-70 , TLC (1: 1EtOAc / Hexane) showed no starting material B2.1L hexane was added while hot, then add a little cold n-hexane 2L stirred at room temperature overnight, filtered to give a white solid with MTBE (3 × 600mL) washing and drying to give 573.8g 3- [2- (1, 3- two isoindoline-one)] propionaldehyde, yield: 94percent.Step 2. Preparation of 3-(l, 3-dioxoisoindolin-2-yl)propanal A mixture of 2-(3-hydroxypropyl)isoindoline-l, 3-dione (2.0 g, 8.76 mmol) and IBX (8.2 g, 29.27 mmol) in 60 mL EA was refluxed for 2 h. The mixture was filtered and filtrate was concentrated to afford 3-(l, 3-dioxoisoindolin-2-yl)propanal (2.0 g , yield: 100percent) as white solid. NMR (500 MHz, CDC1A 50 ml round bottom flask was charged with aq. NaHCO3(0.05 M, 10 ml), aq. K2CO3(0.5 M, 10 ml) and CHCl3(5 ml). Alcohol 5 (16.02 g, 78.1 mmol) was dissolved in CHCl3(50 ml) and transferred to the reaction mixture followed by tetra-nbutylammonium chloride (4.34 g, 15.6 mmol), N-chlorosuccinimide (20.9 g, 156.1 mmol) and TEMPO (2.44 g, 15.6 mmol) and the reaction mixture was stirred vigorously at rt for 4.5 h. The phases were separated and the organic phase was washed with sulfate buffer (100 ml), NaHCO3(100 ml), and brine (100 ml), dried (Na2SO4), filtered and concentrated in vacuo. Purification by flash column chromatography (35percent EtOAc in n-heptane, v/v) gave aldehyde 9 (6.54 g, 38percent) as a white amorphous solid.In a mixed solvent of tetrahydrofuran (12 ml) and acetic acid (4 ml) was dissolved 2-[2-(1, 3-dioxolan-2-yl)ethyl]-1H-isoindole-1, 3(2H)-dione (728 mg, 2.94 mmol), followed by adding thereto a 2M aqueous hydrochloric acid solution (5 ml) at room temperature, and the resulting mixture was stirred at 50°C for 2 hours. <1-11> 3-(l, 3-dioxy-l, 3-dihydro-isoindol-2-yl)-propionaldehyde; The compound of General procedure: [{Rh(cod)}2(μ-Cl)2] (5 μmol), phosphorus ligand (20 μmol), and solvent (6.3 mL) were added to a pressure reactor (25 mL). After addition of formaldehyde (37 percent in H2O, 6 mmol) and substrate (5 mmol) the reaction mixture was purged with nitrogen for several times and heated with stirring (1000 rpm) to the indicated reaction temperature. Once the desired temperature was achieved, H2 was introduced and the reaction mixture was stirred for the indicated reaction time. After cooling to room temperature the gas was released and the reaction mixture was again purged with nitrogen. Dodecane was added as an internal standard and brine in order to separate the phases. The organic phase was finally analyzed by GC.#10;B. EXAMPLE 23

Molecular Weight:203.19
XLogP3:0.9
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:203.058243149
Monoisotopic Mass:203.058243149
Topological Polar Surface Area:54.4
Heavy Atom Count:15
Complexity:276
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes