1-(Chloromethoxy)-2-methoxyethane → HCID 58122810, compound

Temperature

0 °C

10 ml of a tetrahydrofuran (THF) solution of 1.37 g (11 mmol) of 2-methoxyethoxymethyl chloride was added dropwise to 10 ml of a THF solution of 2.01 g (10 mmol) of N-t-butoxycarbonyl-4-hydroxypiperidine (manufactured by Aldrich) and 2.58 g (20 mmol) of diisopropylethylamine at 0° C. in a nitrogen atmosphere. After the addition, the reaction solution was allowed to reach room temperature, and stirred for one hour. After confirming disappearance of the raw materials by thin-layer chromatography (TLC), the reaction solution was cooled to 0° C. The reaction was then terminated by adding water. The reaction solution was subjected to an extraction operation three times using water and ethyl acetate. The resulting organic layer was washed once with a saturated ammonium chloride solution, washed once with water, washed once with a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. After evaporating the solvent under reduced pressure, the product was purified by column chromatography to obtain 1.7 g of N-t-butoxycarbonyl-4-[(2-methoxyethoxy)methoxy]piperidine as a colorless liquid (hereinafter referred to as “compound (A-1)”) (yield: 60%).

1. additionAfter the addition
2. customto reach room temperature
3. customThe reaction was then terminated
4. additionby adding water
5. washThe resulting organic layer was washed once with a saturated ammonium chloride solution
6. washwashed once with water
7. washwashed once with a saturated sodium chloride aqueous solution
8. dry with materialdried over anhydrous sodium sulfate
9. customAfter evaporating the solvent under reduced pressure
10. customthe product was purified by column chromatography

ORD record

ord-750a4c04d33c4844bcd437946f64a8da

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08273521B2