Formic Acid → HCID 58432666, Verbindung

Temperatur

0 °C

Formic acid (65 mL, 17.2 mmol) was added dropwise to neat chlorosulfonyl isocyanate (1.5 mL, 17.2 mmol) at 0° C. with rapid stirring. Vigorous gas evolution was observed during the addition process. The resulting viscous suspension was stirred for 5 min at 0° C. during which time the mixture solidified. Dichloromethane (9 mL) was added and the solution was stirred for 1 h at 0° C. then 8 h at 25° C. The reaction mixture was cooled to 0° C. and a solution of 3-methylpentan-1-ol (11.5 mmol) and pyridine (1.4 mL, 17.2 mmol) in 8 mL of dichloromethane was added dropwise. The contents were warmed to 25° C. and stirred for 3 h. The reaction mixture was treated with EtOAc (80 mL) and water (50 mL), and the aqueous layer was extracted with EtOAc (2×20 mL). The combined organic phase was washed with brine, dried over MgSO4, filtered and then concentrated. The crude product was purified by multiple flash chromatographies (7% ethyl acetate/dichloromethane) to give 3-methylpentyl sulfamate.

1. stirringthe solution was stirred for 1 h at 0° C.
2. custom8 h
3. customat 25° C
4. temperatureThe reaction mixture was cooled to 0° C.
5. temperatureThe contents were warmed to 25° C.
6. stirringstirred for 3 h
7. extractionthe aqueous layer was extracted with EtOAc (2×20 mL)
8. washThe combined organic phase was washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated
12. customThe crude product was purified by multiple flash chromatographies (7% ethyl acetate/dichloromethane)

ORD-Eintrag

ord-2554fcceb0d9452eb8641e073c13b203

Quelldatensatz

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08722727B2