ChemicalBook CAS DataBase List Boc-1-amino-3,6-dioxa-8-octanediamine

Boc-1-amino-3,6-dioxa-8-octanediamine synthesis

10synthesis methods

Product Name:Boc-1-amino-3,6-dioxa-8-octanediamine
CAS Number:153086-78-3
Molecular formula:C11H24N2O4
Molecular Weight:248.32

929-59-9

24424-99-5

153086-78-3

General procedure: A dichloromethane solution (10 mL/mmol) of 1,8-diamino-3,6-dioxaoctane (1 eq.) was treated with di-tert-butyl dicarbonate (0.15 eq.) at 0 °C, kept at 0 °C for 5 hours, and then the reaction was continued at room temperature for 18 hours. Upon completion of the reaction, the organic phase was washed with water until all unreacted 1,8-diamino-3,6-dioxaoctane was removed by extraction. The organic phase was dried over anhydrous magnesium sulfate and recovered quantitatively to give the Boc-protected product tert-butyl 2-(2-(2-aminoethoxy)ethoxy)ethylcarbamate, which was concentrated under vacuum. The product characterization data were as follows:11a: 1H NMR (300 MHz, CDCl3): δ 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2).11b: 1H NMR ( 300 MHz, CDCl3): δ 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).

929-59-9 Synthesis

929-59-9
215 suppliers
$8.00/5g

24424-99-5 Synthesis

24424-99-5
861 suppliers
$13.50/25G

153086-78-3
232 suppliers
$19.00/100mg

Yield:153086-78-3 100%

Reaction Conditions:

in dichloromethane at 0 - 20; for 23 h;Inert atmosphere;

Steps:

1.1. Mono-protection of 10
General procedure: The diamine 10 (1 equiv) in DCM solution (10 mL / mmol) was treated with Boc2O in default (0.15 equiv) for 5 h at 0 °C and 18 h at room temperature. The organic phase was washed with water, until all the unreacted 10 was extracted. The Boc-protected compound 11 was quantitatively recovered after drying (MgSO4) and concentration under vacuum. 11a: 1H NMR (300 MHz, CDCl3): d 1.45 (s, 9H), 1.80 (br m, 2H, NH2), 3.25 (m, 2H), 3.38 (m, 2H), 3.50-3.70 (m, 8H), 5.10 (br s, 1H, NHCO2). 11b: 1H NMR (300 MHz, CDCl3): d 1.42 (s, 9H), 1.75 (br m, 2H, NH2), 2.84 (t, 2H, J = 5.3 Hz), 3.29 (m, 2H), 3.51 (m, 4H), 3.58 (sharp m, 8H), 5.30 (br s, 1H, NHCO2).

References:

Favre, Annaïck;Grugier, Jérôme;Brans, Alain;Joris, Bernard;Marchand-Brynaert, Jacqueline [Tetrahedron,2012,vol. 68,# 52,p. 10818 - 10826] Location in patent:supporting information

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