Реакция #1731306

Уравнение реакции

3-Methyl-isoxazole-4-carboxylic acid

HOBt

EDCI

(R)-1-Amino-1,2,3,4-tetrahydronaphthalene

→

title compound

Выход 62.5%

3-Methyl-isoxazole-4-carboxylic Acid (1,2,3,4-tetrahydro-naphthalen-1-yl)-amide

Выход 62.5%

Растворители

DCM

DMF

Условия реакции

Обработка

1. 1
   ТемператураThe clear yellow solution was cooled to 0 C
2. 2
   workup.STIRRINGwas stirred for overnight
3. 3
   ЭкстракцияDilution with DCM (50 mL) was followed by aqueous extraction (NaHCO3 water, brine (50 mL)
4. 4
   Сушкаdrying over MgSO4, filtration and removal of solvent in vacuo

Методика

To a solution of 3-Methyl-isoxazole-4-carboxylic acid (0.52 g, 4.06 mmol) in DCM (15 mL) and DMF (2 mL), was added HOBt (1.1 g, 8.14 mmol) and EDCI (0.896 g 4.67 mmol). The clear yellow solution was cooled to 0 C and allowed to stir under Ar for 15 minutes. To the solution was added (R)-1-Amino-1,2,3,4-tetrahydronaphthalene (0.73 mL, 5.04 mmol and the reaction mixture was allowed to slowly warm to ambient temperature and was stirred for overnight. Dilution with DCM (50 mL) was followed by aqueous extraction (NaHCO3 water, brine (50 mL), drying over MgSO4, filtration and removal of solvent in vacuo. Silica gel chromatography (0-25% Hexane:EtOAc) afforded the title compound (650 mg; 62.5%) as a sticky solid. 1H NMR (CDCl3) δ 1.88 (m, 3H), 2.12 (m, 1H), 2.51 (s, 3H), 2.81 (m, 2H), 5.32 (m, 1H), 5.99 (bd, 1H), 7.13 (m, 1H), 7.20 (m, 2H) 7.20 (m, 2H); 13C NMR (CDCl3) δ 11.22, 20.15, 29.41, 30.35, 47.93, 116.73, 126.72, 127.88, 128.88, 129.65, 136.25, 138.00, 158.45, 160.28. ESIMS: 257 (M+H) EA calc'd for C15H16N2O2: C, 70.29; H, 6.29; N, 10.93. found C, 70.61; H, 6.11; N, 11.09.

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