95530-58-8, (R)-4-Isopropyloxazolidin-2-one is a oxazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,95530-58-8
Sodium hydride (55% suspension in oil, 144 mg, 3.31 mmol) was added to a solution of (R) -4-isopropyl-2-oxazolidinone (356 mg, 2.75 mmol) in dry tetrahydrofuran (17 mL) under argon atmosphere. The suspension was stirred for 1 hour at rt, then cooled to [0C] and a solution of 1-bromo-3-chloropropane in dry tetrahydrofuran (3 mL) was added dropwise. After 48 h stirring at [58C] the mixture was quenched with water. The solvent was removed by evaporation under reduced pressure and the residue partitioned between water and dichloromethane. The organic layer was evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with a mixture of ethyl acetate and n-Heptane (70: 30), afforded [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (401 mg, 71 %). A solution of [(4R)-3- (3-CHLOROPROPYL)-4-ISOPROPYLOXAZOLIDINON-2-ONE] (160 mg, 0.78 mmol) in dry DMF (2 mL) was added to a suspension of potassium carbonate (217 mg, 1.57 mmol) and N-(4-fluorobenzyl)-2-(4-isobutoxyphenyl)- N-piperidin-4-yl-acetamide 103NLS56 (250 mg, 0.63 mmol) in dry DMF (6 mL). After addition of sodium iodide (113 mg, 0.75 mmol) the mixture was stirred overnight at [62C] and partitioned between water and dichloromethane. The organic layer were dried over sodium sulphate, filtered and evaporated to dryness. Purification of the residue by silica gel column chromatography, eluting with 5% methanol in dichloromethane, afforded the desired compound (143 mg, 40%). Rf = 0.28 [(MEOH/CH2CL2] 6: 96). LCMS m/z 568 [[M+H] +. IH] NMR (CDCl3, rotamers 0.4 : 0.6) 8 7.20-6. 78 (m, 8H, Ar-H), 4.61-4. 51 (m, 0.6H, pip-H), 4.48 & 4.42 (2s, 2H, benzyl-H), 4.15 (t, 1H, J= 8.8, oxa-H), 4.01 (m, 1H, oxa-H), 3.78-3. 64 (m, 4.2H, pip- H, benzyl-H, oxa-H, CH2OiBu), 3.48 (m, 2.2H, benzyl-H, CONCHCH2), 2.92-2. 79 (m, 3H, pip-H, [CONCH2),] 2.34-2. 22 (m, 2H, [NCH2CH2CH2),] 2.10-1. 96 (m, 3.2H, pip-H, CHiPr, [CHOIBU),] 1.76-1. 50 (m, 6H, pip-H, [NCH2CH2),] 1.32-1. 26 (m, 0.8H, pip-H), 0.99 (m, 6H, [CH3OIBU)] 0.81-0. 87 (m, 6H, [CH3IPR). HPLC TR=] 9.1 min.
As the paragraph descriping shows that 95530-58-8 is playing an increasingly important role.
Reference£º
Patent; ACADIA PHARMACEUTICALS INC.; WO2004/808; (2003); A2;,
Oxazolidine – Wikipedia
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