(Diethylamino)sulfur trifluoride → HCID 60067049, compound

HRID 2308109Notes

Reaction equation

HRID 2308109 reaction equation
O[C@H:2]1[C@H:6]([O:7][CH3:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.CCN(S(F)(F)[F:25])CC>C(Cl)Cl>[F:25][CH:2]1[C@H:6]([O:7][CH3:8])[CH2:5][N:4]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 60128538HCID 60128538, compound

Product 1

HCID 60067049HCID 60067049, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of benzyl (3R,4R)-3-hydroxy-4-methoxypyrrolidine-1-carboxylate (0.818 g, 3.26 mmol) in 20 mL CH2Cl2 at −20° C. was added DAST (0.946 mL, 7.16 mmol). The reaction mixture was stirred at −20 ° C. and then room temperature overnight. The reaction mixture was quenched with 30 mL half saturated NaHCO3, stirred at room temperature for 15 min and extracted with EtOAc (2×30 mL). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (25% EtOAc in Hexane) to give pale yellow solid (0.551 g, 67%). 1H NMR (CDCl3) δ 7.36-7.29 (5H, m), 5.13 (2H, s), 5.09, 4.92 (1H, m), 3.95-3.91 (1H, m), 3.74-3.35 (4H, m), 3.37 (3H, s).

Workup

  1. customroom temperature overnight
  2. customThe reaction mixture was quenched with 30 mL half saturated NaHCO3
  3. stirringstirred at room temperature for 15 min
  4. extractionextracted with EtOAc (2×30 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customThe residue was purified by flash column chromatography (25% EtOAc in Hexane)

Sources & evidence

ORD record
ord-1c18f58e9dab4964aa0e9feacc5959fe
Source dataset
uspto-grants-2004_12
Patent number
US06833456B2

Reaction notes

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