تفاعل #2254209

ord-4f8ee84692c44d63b07cae845a39beaa

معادلة التفاعل

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
Cc1ccc(C2(CC=O)CCOC(C)(C)C2)cc1
2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde
Cc1cccc(CN)c1
3-methylbenzylamine
CC(=O)O
acetic acid
Cc1ccc(C2(CCNCc3cccc(C)c3)CCOC(C)(C)C2)cc1
{2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    workup.STIRRINGThe resulting mixture was stirred at rt for 18 h
  2. 2
    تركيزThe mix was concentrated
  3. 3
    workup.DISSOLUTIONdissolved in MeOH
  4. 4
    أخرىpurified by HPLC

الإجراء التجريبي

A mixture of 2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]acetaldehyde (61.6 mg, 0.25 mmol), 3-methylbenzylamine (63 μl, 0.5 mmol) and acetic acid (50 μl, 8.6 mmol) in CH2Cl2 (3 ml) was stirred at rt for 1 h before it adding sodium triacetoxyborohydride (106 mg, 0.50 mmol). The resulting mixture was stirred at rt for 18 h. The mix was concentrated and dissolved in MeOH and purified by HPLC to give {2-[2,2-dimethyl-4-(4-methylphenyl)oxan-4-yl]ethyl}[(3-methylphenyl)methyl]amine as a white solid (35 mg, 40%, m/z: 352.3 [M+H]+ observed).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09044469B2uspto-grants-2015_06