(Diethylamino)sulfur trifluoride → HCID 86707498, compound

HRID 338989Notes

Reaction equation

HRID 338989 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C@H:9]([C:14]2[CH:15]=[N:16][C:17]([Cl:20])=[CH:18][CH:19]=2)[C:10]([F:13])([F:12])[F:11])[CH2:6][C@@H:5]1O)=[N+:2]=[N-:3].C(N(S(F)(F)[F:28])CC)C>ClCCl>[N:1]([C@H:4]1[CH:5]([F:28])[CH2:6][N:7]([C@H:9]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[N:16][CH:15]=2)[C:10]([F:13])([F:12])[F:11])[CH2:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 86707499HCID 86707499, compound

Product 1

HCID 86707498HCID 86707498, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S,4R)-4-azido-1-((R)-1-(6-chloropyridin-3-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ol (2.4 g, 7.5 mmol) in dichloromethane (30 mL) at −78° C., was added diethylaminosulfur trifluoride (1.17 mL, 8.95 mmol). The resulting solution was allowed to warm to ambient temperature and stirred overnight. The mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate and washed with water and brine, then dried (MgSO4), filtered and concentrated. The crude residue was purified by column chromatography (Biotage, 40M; 10-25% ethyl acetate/hexanes gradient) to afford 5-((1R)-1-((3R)-3-azido-4-fluoropyrrolidin-1-yl)-2,2,2-trifluoroethyl)-2-chloropyridine (1.02 g, 42%).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by column chromatography (Biotage, 40M; 10-25% ethyl acetate/hexanes gradient)

Sources & evidence

ORD record
ord-368642cc6648452398e88fcd4eefd9dd
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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