Nitrogen → 2-(4-Methylisoxazol-3-yl)ethanol

A solution of (Z)-3-(tert-butyldimethylsilyloxy)-N-hydroxypropanimidoyl chloride (90 mg, 0.378 mmol) in ClCH2CH2Cl (Volume: 2 mL) at room temperature was purged with N2 for 2 min. Prop-1-yne (0.022 mL, 0.378 mmol) [Condensed at −78° C.] was added as a liquid, followed by chloro(1,5-cyclooctadiene)(pentamethylcyclopentadienyl)ruthenium (II) (7.17 mg, 0.019 mmol) and triethylamine (0.066 mL, 0.473 mmol). The reaction mixture was stirred at room temperature for 16 h. It was dark brown in color. The mixture was filtered through 0.45 μm membrane. The filtrate was concentrated, diluted with MeOH, and purified with prep HPLC (Waters Xbridge C18 19×100 mm), 20 mL/min flow rate with gradient of 30% B-100% B over 10 minutes Hold at 100% B for 2 min. (A: 0.1% TFA in water/MeOH (90:10), B: 0.1% TFA in water/MeOH (10:90) monitoring at 220 nm. After concentration, 2-(4-methylisoxazol-3-yl)ethanol (35 mg, 0.270 mmol, 71.3% yield) was obtained as light brown liquid. 1H NMR (400 MHz, chloroform-d) δ 8.13 (s, 1H), 4.03 (t, J=5.9 Hz, 2H), 2.89 (t, J=5.9 Hz, 2H), 2.02 (d, J=0.9 Hz, 3H).

1. filtrationThe mixture was filtered through 0.45 μm membrane
2. concentrationThe filtrate was concentrated
3. additiondiluted with MeOH
4. custompurified with prep HPLC (Waters Xbridge C18 19×100 mm), 20 mL/min flow rate with gradient of 30% B-100% B over 10 minutes
5. waitHold at 100% B for 2 min.
6. concentrationAfter concentration

ORDレコード

ord-659fba1ad75d4be39ce333bd9879bc45

出典データセット

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09249157B2