تفاعل #426602

معادلة التفاعل

3-Methyl-isoxazole-4-carboxylic acid

HOBt

EDCI

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

→

title compound

المردود 62.5%

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

المردود 62.5%

المذيبات

DCM

DMF

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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.

المصدر