1,1-Cyclopropanedimethanol

Colorless to yellow liquid

Scheme 28; 28-B (1-HYDROXYMETHYL-CYCLOPROPYL)-METHANOL; To a solution OF DIMETHYL 1, 1-CYCLOPROPANEDICARBOXYLATE 28-A (791 mg, 5.01 MMOL) in Et2O (20 mL) at 0°C was added lithium aluminum hydride (569 mg, 15.0 MMOL) portionwise. The reaction mixture was stirred at room temperature for 4 h and quenched with saturated NA2SO4 at 0°C. The precipitated solid was filtered and washed with THF. The filtrate was concentrated and purified by column chromatography (EtOAc) to give 440 mg (86percent) OF 28-B ; 1H NMR (300 MHz, CD13) 8 4.02 (s, 2 H), 3.56 (s, 4 H), 0.48 (s, 4 H); MS (ES) m/z: 125 (M+Na+).The title compound was prepared by dissolving dimethyl cyclopropane-1, 1- dicarboxylate (lOg, 1 eq. ) in 250 mL THF and cooling the mixture to 0°C. To the cooled and stirred mixture 126.5 (2 eq. ) of lithium aluminum hydride (LAH) as a 1 M solution in THF was added. The mixture was heated at reflux for 16 hours. The mixture was cooled to 0°C and quench with a small portion of H20 followed by a small amount of 15percent sodium hydroxide along with additional water and stirred three hours. Filter through glass sintered funnel, rinsing with THF. The solution was concentrated to a clear oil. The title compound was recovered in a 48percent yield (3.095 g).LAH (0.28 g, 7.52 mmol) was dissolved in 10 mL of THF, and the solution was cooled to -18. Diethyl 1, 1-cyclopropanedicarboxylate (1.0 g, 5.37 mmol) in 7 mL of THF was slowly added thereto, and the reaction mixture was stirred for 16 hours at room temperature. 0.3 mL of water and the 0.3 mL of 4M NaOH aqueous solution were added thereto. The mixture was filtered with Celite and purified by column chromatography to obtain the title compound (0.2 g, 35 percent). Step A: To the equipped with a mechanical stirring device of four flasks add previous step prepared in 1, 1 - cyclopropyl acid bis b ester thick 42g (225.56mmol), anhydrous THF 200 ml and lithium chloride 42.35g (998.92mmol), under stirring condition through the ice salt bath then cooling the mixture to 0 °C and maintain the temperature constant, batch adding potassium borohydride 53.88g (998.92mmol), after material feeding is finished, the reaction system heating to reflux, GC monitoring reaction progress, in order to 1, 1 - cyclopropyl ethyl phthalate disappear as the end point of the reaction. After the reaction, the reaction ice salt bath again through cooling to 0 °C, water 200 ml quenching reaction and continue to stir 2h, adding the ethyl acetate extraction (divided into 3 times, each time the 100 ml), the combined organic phase, anhydrous sodium sulfate drying, by reduced pressure distillation to remove the ethyl acetate (can be recycled), by reduced pressure distillation mode, in 4mmHg collected under a pressure condition of the range is the 92 - 95 °C fraction, get colorless viscous liquid 22.45g, is 1, 1 - cyclopropyl b methanol (two-step overall yield 88percent).Step 7 Step 1 Step 1 Step 1

1,1-Bis(hydroxymethyl)cyclopropane is used in the synthesis of morphine alkaloids. It also serves as an inhibitor of 5-lipoxygenase.

Molecular Weight:102.13
XLogP3:-0.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:102.068079557
Monoisotopic Mass:102.068079557
Topological Polar Surface Area:40.5
Heavy Atom Count:7
Complexity:60.5
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes