Ethanolamine → HCID 67416823, compound

A solution of 3 ml (39.6 mmol) of methyl glycolate in 25 ml of tetrahydrofuran is added dropwise over 2 hours to a solution of 49 ml (95 mmol) of phosgene, 1.9M in toluene, which is diluted in 50 ml of tetrahydrofuran and cooled using an ice bath. The mixture is subsequently stirred at ambient temperature for 16 hours and evaporated to dryness. Coevaporation is carried out 4 times with 30 ml of dichloromethane. The residue is taken up with 40 ml of acetonitrile and added dropwise over 1 hour to a solution of 3.4 ml (59.4 mmol) of ethanolamine and 30 ml (178 mmol) of diisopropylethylamine in a 50/10 mixture of acetonitrile and dichloromethane, cooled using an ice bath. The mixture is subsequently stirred at ambient temperature for 16 hours. It is filtered over celite and evaporated to dryness and the product is purified by chromatography on silica gel, eluting with a 70/30 then 80/20 mixture of ethyl acetate and n-hexane, to give 4.9 g of product in white solid form.

1. temperaturecooled
2. customevaporated to dryness
3. temperaturecooled
4. stirringThe mixture is subsequently stirred at ambient temperature for 16 hours
5. filtrationIt is filtered over celite
6. customevaporated to dryness
7. customthe product is purified by chromatography on silica gel
8. washeluting with a 70/30
9. addition80/20 mixture of ethyl acetate and n-hexane

ORD record

ord-e97dde8a1f6148558edae15611003a6e

Source dataset

uspto-grants-2008_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07439257B2