Water → HCID 86602704, compound

Temperature

0 °C

A mixture of triphenylphosphine (10.2 g), diethyl azodicarboxylate (6.12 ml), and (2S)-1-[N-benzyl-N-[(2S)-2-hydroxy-3-methoxypropyl]amino]-3-methoxypropan-2-ol (7.34 g) in tetrahydrofuran (70 ml) was stirred at 0° C. for 5 hours. To the mixture was added successively triphenylphosphine (2.04 g) and diethyl azodicarboxylate (1.2 ml), and the mixture was stirred at 0° C. for 3 hours. The mixture was poured into water and extracted with dichloromethane (×3). The combined extracts were washed with brine, dried over sodium sulfate, and evaporated. Isopropyl ether (50 ml) was added to the residue and stirred at room temperature for 30 minutes. The insoluble precipitate was filtered off, and the solution was evaporated and purified twice with column chromatography (1st: silica gel 800 ml, ethyl acetate:isopropyl ether=2:8–3:7) (2nd: silica gel 300 ml, ethyl acetate:isopropyl ether 3:97–10.90) to give 4-benzyl-cis-2,6-dimethoxymethylmorpholine (2.65 g) as an oil.

1. stirringthe mixture was stirred at 0° C. for 3 hours
2. extractionextracted with dichloromethane (×3)
3. washThe combined extracts were washed with brine
4. dry with materialdried over sodium sulfate
5. customevaporated
6. additionIsopropyl ether (50 ml) was added to the residue
7. stirringstirred at room temperature for 30 minutes
8. filtrationThe insoluble precipitate was filtered off
9. customthe solution was evaporated
10. custompurified twice with column chromatography (1st: silica gel 800 ml, ethyl acetate:isopropyl ether=2:8–3:7) (2nd: silica gel 300 ml, ethyl acetate:isopropyl ether 3:97–10.90)

ORD record

ord-37ccc4754a8f4568811feee24ff41b8a

Source dataset

uspto-grants-2007_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07166598B2