Methyl iodide → HCID 178496656、化合物

温度

0 °C

tert-Butyl(trans-3-hydroxycyclobutyl)carbamate (1.18 g, 6.3 mmol) was dissolved in dry THF (25 mL) under a nitrogen atmosphere, and the solution cooled to 0° C. To this clear solution was added, sodium hydride (60% dispersion in oil, 0.25 g, 6.3 mmol) portion wise (evolution of H2 observed). The reaction mixture was stirred at RT for 30 min. then iodomethane (0.40 mL, 1.5 mmol) added dropwise and the resulting yellow suspension stirred at RT for 16 h. The reaction mixture was quenched with saturated aqueous solution of NH4Cl (20 mL) and partitioned between saturated aqueous solution of NaHCO3 (40 mL) and DCM (60 mL). The combined organic fractions were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was purified by column chromatography (gradient 0-70% EtOAc in cyclohexane) to afford the title compound as a yellow oil (1.05 g, 82%). 1H NMR (CDCl3, 300 MHz): δ 4.65 (1H, br s), 4.22-4.10 (1H, m), 4.00-3.92 (1H, m), 2.40-2.28 (2H, m), 2.18-2.12 (2H, m), 1.43 (9H, s).

1. additionTo this clear solution was added
2. stirringthe resulting yellow suspension stirred at RT for 16 h
3. customThe reaction mixture was quenched with saturated aqueous solution of NH4Cl (20 mL)
4. custompartitioned between saturated aqueous solution of NaHCO3 (40 mL) and DCM (60 mL)
5. washThe combined organic fractions were washed with brine (20 mL)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customThe resulting residue was purified by column chromatography (gradient 0-70% EtOAc in cyclohexane)

ORDレコード

ord-7b713579512c4cccae3794777928c128

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08653089B2