With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.693287-79-5,tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate,as a common compound, the synthetic route is as follows.,693287-79-5
(a) 1 -(tetrahvdro-2H-pyran-4-yl)hydrazineTo a solution of tetrahydropyran-4-one (71 6 g, 715 mmol) in methanol(2 L) was added tert-butylcarbazate (100 g 758 mmol) at ambient temp The mixture was stirred at ambient temp for 20 h The reaction mixture was concentrated under reduced pressure to dryness to afford a white solid (154 g) To a suspension of the white solid ( 154 g, 715 mmol) in water (1 L) was added acetic acid (500 mL, 8 73 mol) and the mixture was stirred for 30 mm to get a clear solution To this solution, solid NaCNBH3 (44 5 g, 708 mmol) was added portion-wise The mixture was stirred at ambient temp for 2 h The mixture was then transferred to a 12 L flask, cooled to 0 C, and quenched with 1 N NaOH (8 73 L 8 73 mol) The mixture was extracted with CH2Cl2 (3 x 3 L) and dried over Na2SO4 The organic layer was filtered and concentrated to afford a white solid (164 g, contains -15% of N-acetyl-N’-Boc-hydrazine derivative) Chromatography [silica, ethyl acetate/MeOH (95 5] gave 94 g of 90% pure boc-hydrazine A solution of boc-hydrazine (50 g, 231 mmol) in methanol (500 mL) was added a solution of HCI in dioxane (462 mL, 1 85 mol, 4 0 M) The mixture was stirred at ambient temp overnight Concentration of the reaction mixture under reduced pressure afforded the title compound as a white solid (43 g 98%) 400 MHz 1 H NMR (DMSO) delta 3 85-3 82 (m, 2H), 3 27-3 21 (m, 2H) 3 13-3 05 (m 1 H) 1 88-1 84 (m 2H), 1 48-1 38 (m 2H) MS (M+H m/z = 1 1 7 2)
693287-79-5 tert-Butyl 2-(tetrahydro-2H-pyran-4-yl)hydrazinecarboxylate 45092245, aTetrahydropyrans compound, is more and more widely used in various.
Reference£º
Patent; PFIZER INC.; WO2008/139293; (2008); A1;,
Tetrahydropyran – Wikipedia
Tetrahydropyran – an overview | ScienceDirect Topics