4-Methylmorpholine → (s)-n-(1-Hydroxymethyl-2-phenylethyl)-1-methyl-2-indolecarboxamide

To a stirred solution of 1-methyl-2-indolecarboxylic acid (100 mg, 0.57 mmol) in methylene chloride (1 mL) was added N-methylmorpholine (0.063 mL, 0.57 mmol) followed by (S)-(−)-2-amino-3-phenyl-1-propanol (86 mg, 0.57 mmol), 1-hydroxybenzotriazole hydrate (81 mg, 0.60 mmol), and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (120 mg, 0.63 mmol). The resulting mixture was stirred at room temperature for 20 h. The reaction was diluted with methylene chloride and washed sequentially with 10% citric acid, saturated NaHCO3, water, and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo to give a crude oil. Trituration of the crude oil with methanol and diethyl ether afforded the title compound (68%, 119.7 mg) as an off-white solid. MS (ES) m/e 309.4 [M+H]+.

1. washwashed sequentially with 10% citric acid, saturated NaHCO3, water, and brine
2. dry with materialThe organic layer was dried over Na2SO4
3. concentrationconcentrated in vacuo
4. customto give a crude oil

ORD 기록

ord-ba43aa1208ed46849711ebd9f4436e12

출처 데이터셋

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US06214856B1