With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1608-26-0,N,N,N’,N’,N”,N”-Hexamethylphosphinetriamine,as a common compound, the synthetic route is as follows.
The ligand precursor HP(OCH2CHi-PrNH)2 (2S,8S)-2,8-isopropyl-4,6-dioxa-1,9-diaza-5lambda5-phosphaspiro[4.4]nonane 1 was obtained using the general procedure described in the literature [9] A mixture of P(NMe2)3 (1.14?cm3, 6.27?mmol) and (S)-(+)-2-amino-3-methyl-butanol (CH3)2CHCH(NH2)CH2OH (0.31?g, 12.6?mmol) and 6?cm3 of toluene was placed in a round-bottomed flask equipped with a magnetic stirrer and a reflux condenser, and then heated gradually to 100?C over 2?h with gentle argon purging. The progress of the reaction was monitored by GC-MS analyses. The crude product (white solid) was purified by recrystallization from hexane in a freezer providing crystals suitable for X-ray analysis. Yield: 1.14?g (78%). Anal. Calc. for C10H23N2O2P: C, 51.27; H, 9.90; N, 11.96 Found: C, 50.82; H, 9.78; N, 11.6%; 1H NMR (CD2Cl2) major epimer 1a: delta 0.80, 0.89 (12H, d, 3J(H, H)?=?7?Hz, CH3), 1.45 (2H, m, CH), 2.87 (4H, m, CH, NH), 3.33 (2H, ddd, 2J(H, H)?=?8.9?Hz, 3J(H, H)?=?5.7?Hz, 3J(P, H)?=?10.00?Hz, CH2), 3.77 (2H, ddd, 2J(H, H)?=?8.9?Hz, 3J(H, H)?=?6.3?Hz, 3J(P, H)?=?11.36?Hz, CH2), 6.74 (1H, d 1J(P, H)?=?741.1?Hz, PH); minor epimer 1b: delta 0.84, 0.90 (12H, d, 3J(H, H)?=?7?Hz, CH3), 1.52 (2H, m, CH), 2.87 (4H, m, CH, NH), 3.48 (2H, ddd, 2J(H, H)?=?8.9?Hz, 3J(H, H)?=?4.9?Hz, 3J(P, H)?=?11.45?Hz, CH2), 3.69 (2H, ddd, 2J(H, H)?=?8.9?Hz, 3J(H, H)?=?6.5?Hz, 3J(P, H)?=?9.71?Hz, CH2), 6.76 (1H, d 1J(P, H)?=?727.3?Hz, PH) 31P {1H} NMR (CD2Cl2) delta – 53.73 (minor signal), -54.16 (major signal) ppm; IR numax(nujol)/cm-1 658vs, 953vs, 988vs, 1050vs, 1156?m nu(C-O-P), 2347?s 2360?s nu(P-H), 3324?s, nu(N-H); ESI-MS: m/z calcd for [M?+?H]+ 236.14 found 236.14; Deltaepsilon223?=?-0.43, 1608-26-0
1608-26-0 N,N,N’,N’,N”,N”-Hexamethylphosphinetriamine 15355, achiral-phosphine-ligands compound, is more and more widely used in various fields.
Reference£º
Article; Skar?y?ska, Anna; Gniewek, Andrzej; Inorganica Chimica Acta; vol. 483; (2018); p. 248 – 251;,
Phosphine ligand
Chiral phosphine ligands in asymmetric synthesis. Molecular structure and absolute configuration of (1,5-cyclooctadiene)-(2S,3S)-2,3-bis(diphenylphosphino)butanerhodium(I) perchlorate tetrahydrofuran solvate