(Diethylamino)sulfur trifluoride → HCID 86731618, compound

HRID 2273099Notes

Reaction equation

HRID 2273099 reaction equation
O[C@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C@@H:4]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[O:19])[CH2:3]1.CCN(S(F)(F)[F:38])CC>C(Cl)Cl>[F:38][C@@H:2]1[CH2:6][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C@@H:4]([C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[O:19])[CH2:3]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86731617HCID 86731617, compound

Product 1

HCID 86731618HCID 86731618, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (2R,4R)-3-(trifluoromethyl)benzyl 4-hydroxy-1-(3-(trifluoromethyl)benzyl)pyrrolidine-2-carboxylate (D8) (200 mg, 0.45 mmol) in DCM (20 ml) cooled at −20° C. was treated with DAST (0.148 ml, 1.11 mmol) and the mixture was first stirred 1 h at −20° C. then 18 hrs at RT. The reaction was quenched with NaHCO3 sat. sol. and the aqueous phase extracted with DCM (3×5 ml), dried over MgSO4 and evaporated. The residue was purified by Biotage SNAP-Si column (25 g) eluting with petroleum ether/EtOAc from 90/10 to 80/20. Collected fractions, after solvent evaporation afforded the title compound (D9) (110 mg)

Workup

  1. custom18 hrs
  2. customat RT
  3. customThe reaction was quenched with NaHCO3 sat. sol.
  4. extractionthe aqueous phase extracted with DCM (3×5 ml)
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customThe residue was purified by Biotage SNAP-Si column (25 g)
  8. washeluting with petroleum ether/EtOAc from 90/10 to 80/20
  9. customCollected fractions, after solvent evaporation

Sources & evidence

ORD record
ord-d1b2b95826a64dca807ac74e26f83afb
Source dataset
uspto-grants-2015_09
Patent number
US09120824B2

Reaction notes

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