Triethylamine → HCID 71743188, compound

To a stirred solution of tert-butyl (RS)-2-(6-chloropyridin-3-yl)-2-hydroxyethyl(2-hydroxyethyl)carbamate (4.68 g) and triethylamine (3.5 ml) in THF (50 ml) at 0-5° C. was added dropwise methanesulfonyl chloride (1.84 ml). The reaction mixture was then stirred at room temperature for 2.5 hours to afford a yellow suspension. The reaction mixture was then filtered to remove triethylamine hydrochloride, washing the filter with THF (10 ml). The filtrate was cooled to 0-5° C. and potassium 2-methyl-2-butoxide (15.6 ml, 1.7 M solution in toluene) was added. The reaction mixture was stirred at room temperature for 15 min and then poured into EtOAc and washed sequentially with water and with saturated brine. The organic phase was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 70% EtOAc in hexanes) to afford tert-butyl (RS)-2-(6-chloropyridin-3-yl)morpholine-4-carboxylate (1.16 g, 26%) as a yellow solid. MS (ISP): 301.2 ([{37Cl}M+H]+), 299.1 ([{35Cl}M+H]+), 245.2 ([{37Cl}M+H—C4H8]+), 243.2 ([{35Cl}M+H—C4H8]+).

1. customto afford a yellow suspension
2. filtrationThe reaction mixture was then filtered
3. customto remove triethylamine hydrochloride
4. washwashing the
5. filtrationfilter with THF (10 ml)
6. temperatureThe filtrate was cooled to 0-5° C.
7. additionpotassium 2-methyl-2-butoxide (15.6 ml, 1.7 M solution in toluene) was added
8. stirringThe reaction mixture was stirred at room temperature for 15 min
9. additionpoured into EtOAc
10. washwashed sequentially with water and with saturated brine
11. dry with materialThe organic phase was dried over Na2SO4
12. concentrationconcentrated in vacuo
13. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 70% EtOAc in hexanes)

ORD record

ord-2eae443d9a404df6aaf6c07a87787873

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08802673B2