(Diethylamino)sulfur trifluoride → Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamate

HRID 1852190Notes

Reaction equation

HRID 1852190 reaction equation
O[CH2:2][C:3]1([S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7])[CH2:5][CH2:4]1.CCN(S(F)(F)[F:23])CC>C(Cl)Cl>[F:23][CH2:2][C:3]1([S:6]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])(=[O:8])=[O:7])[CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 57816716HCID 57816716, compound

Product 1

HCID 70978761Tert-butyl 1-fluoromethylcyclopropylsulfonylcarbamateYield 72.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 1-hydroxymethylcyclopropylsulfonylcarbamate (26 g, 103 mmol) in DCM (300 mL) was cooled to −78° C. To this solution was added DAST (41 mL, 310 mmol) and the reaction mass was stirred at the same temperature for 30 min. The reaction mass was quenched with aqueous 1N NaOH solutions. The organic layer was separated and the aqueous layer was acidified to pH ˜2 by using 1.5 N HCl solutions. The aqueous solution was extracted with DCM (50 mL×4). The combined organic layer was dried over anhydrous sodium sulphate and evaporated to get desired compound (19 g, 72%) as gummy mass. 1H NMR (400 MHz, DMSO-d6): δ ppm 11.25 (sb, 1H), 4.75 (s, 1H), 4.63 (s, 1H), 1.44 (s, 9H), 1.28 (m, 2H), 1.07 (m, 2H). 19F NMR: −211.7 (1F).

Workup

  1. customThe reaction mass was quenched with aqueous 1N NaOH solutions
  2. customThe organic layer was separated
  3. extractionThe aqueous solution was extracted with DCM (50 mL×4)
  4. dry with materialThe combined organic layer was dried over anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-d05ba2f8c5084439a66aaeed37dd4dc6
Source dataset
uspto-grants-2015_02
Patent number
US08957203B2

Reaction notes

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