Hydrochloric Acid → N-(Tert-butyl)-1-(fluoromethyl)cyclopropane-1-sulfonamide

Temperature

0 °C

To a round-bottom flask equipped with a stir bar was added N-(tert-butyl)-1-(hydroxymethyl)cyclopropane-1-sulfonamide (8.66 g, 41.8 mmol) and CH2Cl2 (110 mL). The stirred solution was cooled to 0° C. and to the solution was added (diethylamino)sulfur trifluoride (11 mL, 84 mmol). The solution was allowed to warm to room temperature with stirring for 4 h. The solution was then slowly added to a stirred sat. aq. sodium bicarbonate (100 mL) and following the addition stirring was maintained for 18 h. The pH of the aqueous phase was adjusted to pH=4 using aq. HCl. The mixture was transferred to a separatory funnel and was twice extracted with CH2Cl2. The combined organics were washed with brine; dried over MgSO4; filtered; and then concentrated in vacuo to afford a brown solid residue. This material was subjected to SiO2 chromatography (hexanes:EtOAc, 90:10 to 40:60) to afford N-(tert-butyl)-1-(fluoromethyl)cyclopropane-1-sulfonamide as a colorless, crystalline solid (5.66 g, 65%). 1H NMR (400 MHz, CDCl3) δ 4.73 (s, 1H), 4.60 (s, 1H), 4.22 (br. s., 1H), 1.59-1.53 (m, 2H), 1.37 (s, 9H), 1.12-1.07 (m, 2H).

1. customTo a round-bottom flask equipped with a stir bar
2. temperatureto warm to room temperature
3. additionthe addition
4. stirringstirring
5. temperaturewas maintained for 18 h
6. customThe mixture was transferred to a separatory funnel
7. extractionwas twice extracted with CH2Cl2
8. washThe combined organics were washed with brine
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationand then concentrated in vacuo
12. customto afford a brown solid residue

ORD record

ord-53969ef9231d4ea8aa203c30ca311330

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957203B2