(cyclopropylmethyl)(2,2-dimethoxyethyl)amine synthesis

Yield:1104193-66-9 61%

Reaction Conditions:

with sodium tris(acetoxy)borohydride;acetic acid in methanol at 20; for 24 h;

Steps:

5.1

A solution of cyclopropanecarboxaldehyde in MeOH (0.2 M) was treated with 2,2- dimethoxyethylamine (1.2 eq). The solution was cooled with an ice/water bath and treated portionwise with NaCNBH₃ (1.0 eq). The pH of the resulting solution was adjusted to 6 with AcOH, and the reaction left at RT for 24 h. The mixture was concentrated, diluted with EtOAc, washed with sat. aq. NaHCO₃, brine, dried (Na₂SO₄), filtered and concentrated in vacuo to afford the product (61 %). ¹R NMR (300 MHz, DMSO-J₆, 300 K) δ 0.05-0.07 (m, 2H), 0.15-0.17 (m, 2H), 0.87-0.93 (m, IH), 2.39-2.41 (m, 2H), 2.64-2.66 (m, 2H), 3.3 (s, 6H), 4.46 (t, J 3.0, IH), 5.38 (m, IH).

References:

WO2009/10783,2009,A1 Location in patent:Page/Page column 33