Ethanolamine → 4-Acetoxybenzyl 2-hydroxyethylcarbamate

A solution of butyl chloroformate (250 μL, 2 mmol) in 7 mL of CH2Cl2 was added to a mixture of ethanolamine (140 μL, 2.3 mmol) and triethylamine (540 μL, 3.9 mmol) in 7 mL of CH2Cl2 cooled in an ice bath. The mixture was stirred in the same bath, which was left unmaintained. After 5 h, it was diluted with 100 mL of ethyl acetate and washed with 50 mL of each of 1% HCl in 2/3 saturated brine, 2/3 saturated brine and saturated aqueous NaHCO3 (twice). The organics were dried over Na2SO4 and concentrated in vacuo to furnish 62 (318 mg, 2 mmol, quant.) as an oil. 1H NMR (400 MHz, CDCl3) δ 0.93 (t, J=7.4 Hz, 3H), 1.37 (sextet, J=7.4 Hz, 2H), 1.59 (pentet, J=7.2 Hz, 2H), 2.25 (broad s, 1H), 3.34 (broad q, J=5.2 Hz, 2H), 3.72 (broad q, J=4.8 Hz, 2H), 4.06 (t, J=6.6 Hz, 2H), 5.05 (broad s, 1H).

1. temperaturecooled in an ice bath
2. waitwas left unmaintained
3. washwashed with 50 mL of each of 1% HCl in 2/3 saturated brine, 2/3 saturated brine and saturated aqueous NaHCO3 (twice)
4. dry with materialThe organics were dried over Na2SO4
5. concentrationconcentrated in vacuo

ORD record

ord-2b65a88c386a42d08e9b1587e0658f0b

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08524691B2