Toluene → N-Cbz-N-methyl-2-aminoethanol

To a stirred and cooled (0° C.) solution of N-methyl ethanolamine (3.10 g, 41.27 mmol), Et3N (11.80 mL, 84.66 mmol) in DMF—H2O (3:1, v/v, 40 mL) was added dropwise 30% toluene solution of benzyl chloroformate (25.40 g, 49.13 mmol) for over 15 min. The resulting mixture was stirred for 1 day at room temp. The mixture was extracted with EtOAc. The extract was washed with sat. NaHCO3, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with n-hexane:EtOAc (3:1, v/v) then CHCl3 as eluent to give 4.67 g (54%) N-methyl-N-(benzyloxy carbonyl)ethanolamine as a colorless oil. 1H-NMR (CDCl3) d 1.82 (bs, 1 H), 3.00 (s, 3 H), 3.46 (bs, 2 H), 3.77 (bs, 2 H), 5,13 (s, 2 H), 7.29-736 (m, 5 H).

1. stirringThe resulting mixture was stirred for 1 day at room temp
2. extractionThe mixture was extracted with EtOAc
3. washThe extract was washed with sat. NaHCO3, brine
4. dry with materialdried over Na2SO4
5. customevaporated
6. customThe residue was purified by column chromatography on silica-gel with n-hexane:EtOAc (3:1

ORD record

ord-c829b60eadb74448881e1383d8c660aa

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756378B2