DR ANTHONY MELVIN CRASTO,WorldDrugTracker, helping millions, A 90 % paralysed man in action for you, I am suffering from transverse mylitis and bound to a wheel chair, With death on the horizon, nothing will not stop me except God................DR ANTHONY MELVIN CRASTO Ph.D ( ICT, Mumbai) , INDIA 25Yrs Exp. in the feld of Organic Chemistry,Working for GLENMARK GENERICS at Navi Mumbai, INDIA. Serving chemists around the world. Helping them with websites on Chemistry.Million hits on google, world acclamation from industry, academia, drug authorities for websites, blogs and educational contribution
Showing posts with label 1-diphenylpentan-2-yl]pyrrolidine-2-carboxamide. Show all posts
Showing posts with label 1-diphenylpentan-2-yl]pyrrolidine-2-carboxamide. Show all posts

Saturday 6 September 2014

(S)-N-[(S)-1-Hydroxy-4-methyl-1,1-diphenylpentan-2-yl]pyrrolidine-2-carboxamide

Reaction scheme


(S)-N-[(S)-1-Hydroxy-4-methyl-1,1-diphenylpentan-2-yl]pyrrolidine-2-carboxamide (5) is obtained as a single isomer (by 1H and 13C NMR) and has the following physical and spectroscopic properties: mp 197-199 °C; [a]D20 -51.6 (1.00, CHCl3
lit.: [a]D25 -46 (c 1.2, CHCl3)]; 
Org. Lett20068, 4097-4099

1H NMR pdf(CDCl 3, 600 MHz) 
d: 0.86 (d, = 6.7 Hz, 3 H), 0.91 (d, J= 6.5 Hz, 3 H), 1.19-1.25 (m, 2 H), 1.42-1.49 (m, 2 H), 1.54-1.59 (m, 3 H), 1.86-1.92 (m, 2 H), 2.56 (dt, J = 10.0, 6.1 Hz, 1 H), 2.82 (dt, J = 9.9, 6.4 Hz, 1 H), 3.48 (dd, J = 9.3, 4.2 Hz, 1 H), 4.58 (t, J = 9.8 Hz, 1 H), 5.45 (br. s, 1 H), 7.12 (t, = 7.3 Hz, 1 H), 7.18 (t, = 7.4 Hz, 1 H), 7.24 (t,= 7.5 Hz, 2 H), 7.30 (t, = 7.6 Hz, 2 H), 7.55 (t, = 7.6 Hz, 4 H), 7.94 (d, = 8.0 Hz, 1 H); 







13C NMR pdf(CDCl 3, 150 MHz) d: 21.5, 23.8, 25.3, 25.7, 30.4, 37.5, 46.9, 56.5, 60.2, 80.8, 125.6, 125.7, 126.3, 126.5, 127.8, 128.1, 145.1, 146.5, 175.9; 

IR (ATR): 3466, 3275, 3069, 2955, 2868, 1634, 1513, 1494, 1446, 1100, 1060, 885, 744 (s), 700 (s), 640 cm-1;


 Anal. Calcd for C23H30N2O2: C, 75.37; H, 8.25; N, 7.64. Found: C, 75.55; H, 7.98; N, 7.74. 


established the enantiomeric purity of 5 thus obtained by conversion into (+)- and (–)-MTPA amides Several sets of diagnostic peaks are observed without cross-over, proving the enantiomeric purity of the final product 5. [MTPA amide derived from (+)-MTPACl: 1H NMR (CDCl3, 600 MHz) d: 0.90 (d, J = 6.9 Hz, 3 H, (CH3)2CH-)), 1.07 (d, J = 6.4 Hz, 3 H, (CH3)2CH-)), 3.60 (s, 3 H, CH3O-); MTPA amide derived from (–)-MTPACl: 1H NMR (CDCl3, 600 MHz) d: 0.89 (d, J = 6.6 Hz, 3 H, (C H3)2CH-)), 0.98 (d, J = 6.4 Hz, 3 H, (CH3)2CH-)), 3.70 (s, 3H, CH3O-).


v91p0137-1.gif






see

 Pure (S)-2-amino-4-methyl-1,1-diphenylpentan-1-ol (2) can be obtained by recrystallization from EtOAc and has the following physical and spectroscopic properties: colorless crystals; mp 134-137 °C; [a]D20-91.6 (1.00, CHCl3) lit.: [a]D25 -96.6 (c 1.00, CHCl3)]; 

Zhou, Z.; Guo, Y. Synth. Commun. 200838, 684-696


1H NMR pdf(CDCl3,600 MHz) d: 0.87 (d, = 6.4 Hz, 3 H), 0.89 (d, = 6.4 Hz, 3 H), 1.06-1.11 (m, 1 H), 1.27 (ddd, J = 14.3, 10.4, 3.8 Hz, 1 H), 1.54-1.59 (m, 1 H), 2.31 (brs, 3 H), 3.98 (d, J = 10.4 Hz, 1 H), 7.14-7.19 (m, 2 H), 7.27 (t, = 7.4 Hz, 2 H), 7.31 (t, = 7.7 Hz, 2 H), 7.48 (d, = 6.8 Hz, 2 H), 7.61 (d, = 7.6 Hz, 2 H); 


13C NMR pdf(CDCl3, 150 MHz) d: 21.3, 24.0, 25.3, 39.4, 54.5, 79.1, 125.5, 125.8, 126.3, 126.6, 128.0, 128.4, 144.5, 147.1;

 IR (ATR): 3337, 3264, 2953, 2866, 1586, 1490, 1469, 1448, 1384, 1181, 1057, 1005, 903, 743 (s), 695 (s), 639 cm-1

Anal. Calcd. for C18H23NO: C, 80.26; H, 8.61; N, 5.20. Found: C, 80.36; H, 8.82; N, 5.15.