Hexane → HCID 57294432, compound

To a solution of (R)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-pyrazine (5.53 g, 30 mmol) in anhydrous THF (80 ml) a 1.6M solution of n-BuLi in hexane (10.85 ml, 17.36 mmol) was added at -78° C. After 30 minutes a solution of bromomethyl methyl ether (4.5 g, 36 mmol) in THF (20 ml) was added dropwise. The reaction mixture was allowed to come to 20° C. overnight and was quenched by addition of 1M phosphate buffer (pH 7, 80 ml). The turbid mixture was stirred for 10 minutes, diluted with water (250 ml) and diethyl ether (180 ml). The layers were separated and the aqueous phase extracted with diethyl ether (2×150 ml). The combined organic layer was dried (Na2SO4), concentrated and purified by flash chromatography (silica gel; hexane:diethyl ether 5:1) to yield 5.61 g. To remove final impurities of the other diastereomer the material was crystallized from acetonitrile at -30° C. and the cold precipitate redissolved in CH2Cl2, dried (Na2SO4) and concentrated.

1. customwas quenched by addition of 1M phosphate buffer (pH 7, 80 ml)
2. additiondiluted with water (250 ml) and diethyl ether (180 ml)
3. customThe layers were separated
4. extractionthe aqueous phase extracted with diethyl ether (2×150 ml)
5. dry with materialThe combined organic layer was dried (Na2SO4)
6. concentrationconcentrated
7. custompurified by flash chromatography (silica gel; hexane:diethyl ether 5:1)
8. customto yield 5.61 g
9. customTo remove final impurities of the other diastereomer the material
10. customwas crystallized from acetonitrile at -30° C.
11. dissolutionthe cold precipitate redissolved in CH2Cl2
12. dry with materialdried (Na2SO4)
13. concentrationconcentrated

ORD record

ord-d25272f25f884a689a4d32f69e45cf94

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629293