1,1-Dichloroethane → HCID 59204268, compound

Reaction equation

[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[N:17]=[CH:18][C:19]([CH:22]=O)=[N:20][CH:21]=3)[N:12]=2)=[CH:7][CH:6]=1)[CH:2]([CH3:4])[CH3:3].[CH2:24]([O:26][C:27]([C@H:29]1[CH2:32][C@@H:31]([NH2:33])[CH2:30]1)=[O:28])[CH3:25].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClC(Cl)C>>[CH2:24]([O:26][C:27]([CH:29]1[CH2:32][CH:31]([NH:33][CH2:22][C:19]2[CH:18]=[N:17][C:16]([C:13]3[N:12]=[C:11]([C:8]4[CH:9]=[CH:10][C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])=[CH:6][CH:7]=4)[O:15][N:14]=3)=[CH:21][N:20]=2)[CH2:30]1)=[O:28])[CH3:25]

Participants

Reactant 4

HCID 63651,1-Dichloroethane

HCID 5049666Sodium triacetoxyborohydride

HCID 59204300HCID 59204300, compound

HCID 178472513HCID 178472513, compound

Product 1

HCID 59204268HCID 59204268, compound

Procedure

A solution of 5-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]pyrazine-2-carbaldehyde (0.100 g, 0.32 mmol), cis-3-amino-cyclobutanecarboxylic acid ethyl ester (0.056 g, 0.388 mmol), sodium triacetoxyborohydride (0.082 g, 0.388 mmol) and dichloroethane (5.0 mL) was stirred at room temperature for 12 hours. The reaction mixture was quenched with 1N NaOH (10 mL) and the organic layer was isolated, washed with H2O (2×10 mL) and brine (10 mL), dried (Na2SO4), filtered and concentrated in vacuo to yield the title compound as a crude solid.