(Diethylamino)sulfur trifluoride → HCID 58483851, compound

HRID 732350Notes

Reaction equation

HRID 732350 reaction equation
C(N(S(F)(F)[F:7])CC)C.[CH3:10][O:11][C:12]([C@H:14]1[CH2:18][C@@H:17](O)[CH2:16][N:15]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:13]>ClCCl>[CH3:10][O:11][C:12]([C@H:14]1[CH2:18][C@H:17]([F:7])[CH2:16][N:15]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:13]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 58483851HCID 58483851, compoundYield 104.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add (diethylamino)sulfur trifluoride (3.9 mL, 29.8 mmol) to a −78° C. cooled solution of 4-(R)-hydroxypyrrolidine-N1,2-(R)-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (3.81 g, 15.54 mmol) in dichloromethane (50 mL). Stir 2 h, then remove cold bath and stir 40 h at room temperature. Cool in ice bath and add saturated sodium bicarbonate solution. Warm to room temperature, dry (magnesium sulfate), concentrate (350 mbar, 25° C.) and purify (silica gel chromatography, eluting with diethyl ether and dichloromethane) to give the title compound as an oil (4.01 g, 97%).

Workup

  1. customremove cold bath
  2. stirringstir 40 h at room temperature
  3. temperatureCool in ice bath
  4. additionadd saturated sodium bicarbonate solution
  5. dry with materialdry (magnesium sulfate)
  6. concentrationconcentrate (350 mbar, 25° C.)
  7. custompurify
  8. wash(silica gel chromatography, eluting with diethyl ether and dichloromethane)

Sources & evidence

ORD record
ord-b2367cc3fa1e41fe8d3710da3f2e2bf2
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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