tert-butyl N-(1-ethoxy-3-hydroxypropan-2-yl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of tert-butyl (1-ethoxy-3-hydroxypropan-2-yl)carbamate (2.2 g, 9.4 mmol) in DCM (40 mL) was added methanesulfonylchloride (2.10 g, 18.8 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 12 hours, the reaction mixture was concentrated under reduced pressure. The residue was purified via chromatography on silica gel to afford 2-[(tert-butoxycarbonyl)amino]-3-ethoxypropyl methanesulfonate. MS ESI calc'd. for C11H24NO6S [M+H]+ 298. found 298. 1H NMR (400 MHz, CDCl3) δ 4.95 (s, 1H), 4.28 (d, J=8.0 Hz, 1H), 4.13-4.11 (m, 1H), 3.58-3.48 (m, 5H), 3.03 (s, 3H), 1.45 (s, 9H), 1.18 (t, J=6.8 Hz, 3H). the reaction mixture was concentrated under reduced pressure The residue was purified via chromatography on silica gel

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl N-(tert-butoxycarbonyl)-O-ethylserinate (2.7 g, 10.9 mmol) in THF (40 mL) was added lithium aluminum hydride (0.84 g, 22 mmol) at 0° C. The reaction mixture was allowed to warm to ambient temperature. After 1 hour, the reaction mixture was diluted with water, filtered, and concentrated under reduced pressure to give tert-butyl (1-ethoxy-3-hydroxypropan-2-yl)carbamate which was used without further purification. MS ESI calc'd. for C10H22NO4 [M+H]+ 220. found 220. 1H NMR (400 MHz, CDCl3) δ 5.21 (s, 1H), 3.78-3.59 (m, 3H), 3.58-3.56 (m, 2H), 3.52-3.45 (m, 2H), 1.44 (s, 9H), 1.18 (t, J=6.8 Hz, 3H). filtered concentrated under reduced pressure