반응 #7265

ord-30602e1a95384396af94ffad27829b43

반응 방정식

Cc1ncccc1C=O
2-methyl-pyridine-3-carbaldehyde
NCc1ccc(CN(Cc2nc3ccccc3[nH]2)C2CCCc3cccnc32)cc1
N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine
CC(=O)O
AcOH
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
NaBH(OAc)3
Cc1ncccc1CO
desired product
수율 151.9%
Cc1ncccc1CO
(2-methyl-pyridin-3-yl)-methanol
수율 151.9%

용매

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    기타Purification of the crude white foam (280 mg) by column chromatography on silica gel (200:3:1—CH2Cl2:MeOH:NH4OH)

실험 절차

Using General Procedure B: To a stirred solution of 2-methyl-pyridine-3-carbaldehyde (75 mg, 0.62 mmol), N′-(1H-benzimidazol-2-ylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (246 mg, 0.62 mmol) and AcOH (40 uL, 0.62 mmol) in THF (6.2 mL) was added NaBH(OAc)3 (394 mg, 1.86 mmol) and the mixture was stirred at room temperature overnight. Purification of the crude white foam (280 mg) by column chromatography on silica gel (200:3:1—CH2Cl2:MeOH:NH4OH) afforded the desired product (116 mg, 37%) as a colorless syrup.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US07084155B2uspto-grants-2006_08