Reaction #7269

Reaction equation

N-(tert-butoxycarbonyl)-D-prolinal

N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

sodium triacetoxyborohydride

→

(1H-Benzoimidazol-2-ylmethyl)-(4-{[(pyrrolidin-2-ylmethyl)-amino]-methyl}-benzyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amine

Solvents

CH2Cl2

Conditions

Workup

1. 1
   workup.STIRRINGthe mixture stirred overnight at room temperature
2. 2
   OtherPurification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1)
3. 3
   Otherafforded the more polar mono-alkylated (77 mg, 23%)

Procedure

Using General Procedure B: To a stirred solution of N-(tert-butoxycarbonyl)-D-prolinal (0.121 g, 0.61 mmol) in dry CH2Cl2 (9 mL) was added N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (0.236 g, 0.59 mmol) at room temperature and the mixture stirred for 40 min. To the resultant mixture was added sodium triacetoxyborohydride (0.174 g, 0.82 mmol) and the mixture stirred overnight at room temperature. Purification and separation of the crude material by radial chromatography on a 2 mm TLC grade silica gel plate (CH2Cl2/MeOH/NH4OH, 50:1:1) afforded the more polar mono-alkylated (77 mg, 23%) and the less polar dialkylated (70 mg, 21%) products, both as white foams.

Source