ChemicalBook CAS DataBase List BIS- BOC-SPERMIDINE

BIS- BOC-SPERMIDINE synthesis

12synthesis methods

Product Name:BIS- BOC-SPERMIDINE
CAS Number:68076-39-1
Molecular formula:C17H35N3O4
Molecular Weight:345.48

3-BOC-(4-BOC-AMINOBUTYL)AMINOPROPANENITRILE

68076-41-5
2 suppliers
inquiry

68076-39-1
48 suppliers
$82.50/25 mg

Yield: 100%

Reaction Conditions:

with sodium hydroxide;hydrogen;nickel in ethanol at 30; under 2250.23 Torr; for 18 h;

Steps:

1.d
(d) Hydrogenation of 2-[N-butggyca_rbanYl-y-(4-bntoxvcarbgnYlanfnobutyl)- amino] ethyl cyanide; Raney Nickel (~2.5g) was added to a solution of the product of step (c) (8g) in a 1M ethanolic solution of sodium hydroxide (507ml) in a hydrogenation vessel. The vessel was sealed, purged with nitrogen (3 times) and then with hydrogen (3 times). The reactor was charged with hydrogen (3bar) and stirred at 3bar hydrogen at 30°C for 18 hours. The reaction mixture was combined with a previous batch (3g) and the mixture evaporated down under reduced pressure to -200ml. Water (400ml) was added and the aqueous layer was extracted with chloroform (3 x 250ml). The combined organic layers were dried (anhydrous sodium sulphate), filtered and evaporated down, under reduced pressure to give 2-[N-butoxycarbonyl-N-(4-butoxycarbonylaminobutyl)- amino] propylamine, as a clear oil (11.05 g for combined reactions, quantitative yield). Analysis: 1H-NMR (300MHz, CDCl3) 1.31 (1H, br s, NH), 1.45 (18H, m, 2-But), 1.53 (4H, m, CH2), 1.64 (2H, m, CH2), 2.69 (2H, m, CH2), 3.14 (6H, m, 3 CH2); 1³C-NMR (75MHz, CDCl3) 27.40,28.38, 28.43,39.34, 40.16,46.47, 78.99, 155.96.

References:

HUNTER-FLEMING LIMITED WO2005/116050, 2005, A1 Location in patent:Page/Page column 31

24424-99-5 Synthesis