Methyl iodide → Tert-butyl methyl(pent-4-yn-1-yl)carbamate

A 500 mL round bottom flask was charged with pent-4-ynyl-carbamic acid tert-butyl ester (5.0 g, 27.3 mmol) and tetrahydrofuran (138 mL) and the resulting mixture cooled with an ice/water bath. Sodium hydride (830 mg, 32.9 mmol) was added in 3 portions and the resulting mixture stirred at room temperature for 20 minutes. Methyl iodide (8.6 mL, 138.1 mmol) was slowly added and the resulting mixture stirred for 72 h. The resulting mixture was diluted with dichlormethane (350 mL), washed with 1N HCl (100 mL), 1N, NaOH (100 mL), and water (100 mL). The organic layer was washed with MgSO4, filtered, then concentrated in vacuo to yield methyl-pent-4-ynyl-carbamic acid tert-butyl ester. 1H NMR (300 MHz, CDCl3) δ 3.31 (t, J=7.0 Hz, 2H), 2.86 (s, 3H), 2.17-2.24 (m, 2H), 1.96 (s, 1H), 1.72-1.79 (m, 2H), and 1.46 (s, 9H).

1. temperaturethe resulting mixture cooled with an ice/water bath
2. stirringthe resulting mixture stirred for 72 h
3. washwashed with 1N HCl (100 mL), 1N, NaOH (100 mL), and water (100 mL)
4. washThe organic layer was washed with MgSO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD-Eintrag

ord-8f595ff3b0c5464db78860c371666c5f

Quelldatensatz

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08552032B2