Dichloromethane → HCID 86701855, compound

HRID 1844094Notes

Reaction equation

HRID 1844094 reaction equation
O[C@@H:2]1[C@H:13]2[C@H:9]([N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](=[O:14])[CH2:12]2)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.ClCCl.C(N(S(F)(F)[F:31])CC)C>>[F:31][C@H:2]1[C@H:13]2[C@H:9]([N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:11](=[O:14])[CH2:12]2)[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 123472(Diethylamino)sulfur trifluorideHCID 86701854HCID 86701854, compound

Product 1

HCID 86701855HCID 86701855, compound

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl (3aR,4R,8bS)-4-hydroxy-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (0.200 g, 0.691 mmol) in dichloromethane (1 equiv., 3 mL, 0.69 mmol) was added at 0° C. diethylaminosulfur trifluoride (0.913 mL, 6.91 mmol). The solution was stirred at 0° C. for 30 min. The reaction mixture was carefully quenched with NaHCO3 sat. and extracted with dichloromethane. The organic layer was dried and concentrated. The residue was purified by flash chromatography (0-80% ethyl acetate in cyclohexane) to give the desired product F28 (0.150 g, 74%). LCMS (method A): 1.65 min; ES+: 605 (2M+Na+).

Workup

  1. customThe reaction mixture was carefully quenched with NaHCO3 sat.
  2. extractionextracted with dichloromethane
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (0-80% ethyl acetate in cyclohexane)

Sources & evidence

ORD record
ord-6eb17fdcd6a6429daf1815a1fd2e8ce5
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

Loading…