2-Methylene-1,3-propanediol

clear colorless to pale yellow viscous liquid

General procedure: Allyl alcohol (1 equiv.) and acetic anhydride (1.2 equiv.) were dissolved in DCM (-1M) at 0°C. Pyridine (1 equiv.) and DMAP (0.1 molpercent) were then added. The reaction mixture was stirred at 0 °C for 30 mm. and was then allowed to reach room temperature. After completion, the mixture was quenched with 2N HCI and the organic layer was washed with H20, brine and was dried over Na2SO4. Careful evaporation of the remaining solvents affords the pure compound without further purification.; 2-methylenepropane-1, 3-diyl diacetate (2d). Prepared by general procedure B with the following notes:Column chromatography (hexanes — ethyl acetate 20:1) affords the titled compound as a colorless oil (20g , 91 percent). Analytical data are identical to those in the reference.14General procedure: Allyl alcohol (1 equiv.) and di-ter-butyl dicarbonate (1 equiv.) was dissolved in THF (-1M or neat). DMAP (0.1 molpercent) was added, and then the solution was gently heated using a heat gun until effervescence was observed. After completion (as determined by no more effervescence observed), the mixture was filtered through a silica plug, and the solvent was evaporated. Vacuum distillation or column chromatography (hexanes — ethyl acetate) affords the pure product.; di-tert-butyl (2-methylenepropane-1 , 3-diyl) bis(carbonate) (2e). Prepared by general procedure A with the following notes: Column chromatography (hexanes — ethyl acetate 10:1) affords the titled compound as white crystals (11 g, 98percent). Analytical data are identical to those in the reference.12Preparation of {3-[4-(cyclohexylamino)-l -ethyl- lH-pyrazolo [3, 4-l pyridin- 5-yl]-4, 5-dihydroisoxazole-5, 5-diyl|dimethanol (Compound No. 1)Methylene-l, 3-propane-diol (0.07 ml, 0.00084 mol) was added to the solution of 4- cyclohexylamino-1 -ethyl- lH-pyrazo Io [3, 4-b] pyridine-5-carbaldehyde oxime (121 mg, 0.00042 mol) (example 8) in tetrahydrofuran (5 ml), and the resulting reaction mixture was stirred at room temperature. Sodium hypochlorite (2 ml) was added slowly to the mixture thus obtained over the period of about 5 minutes and the reaction mixture was allowed to stir at room temperature for about 14 hours. Tetrahydrofuran was evaporated off and the organic compound was extracted with ethyl acetate twice. The organic layer was concentrated and purified by column chromatography to yield the title compound.Yield: 41 mg (26percent) m/z: (M++l) 374.39NMR: (delta, CDCl3): 1.26-2.13 (m, 13H), 3.49 (s, 2H), 3.75 (s, 4H), 4.11-4.13 (m, IH), 4.44- 4.49 (q, 2H) 7.99 (s, IH), 8.12 (s, IH).

Used as pharmaceutical intermediate

Molecular Weight:88.11
XLogP3:-0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:88.052429494
Monoisotopic Mass:88.052429494
Topological Polar Surface Area:40.5
Heavy Atom Count:6
Complexity:43.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes