(Diethylamino)sulfur trifluoride → HCID 118207434, compound

HRID 1507229Notes

Reaction equation

HRID 1507229 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[CH2:11][CH2:10][CH:9]([N:12]3[CH2:17][CH2:16][C@@H:15]([C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)[C@H:14](O)[CH2:13]3)[C:8]2=[O:27])=[CH:4][CH:3]=1.CCN(S(F)(F)[F:36])CC>C(Cl)Cl>[F:36][C@H:14]1[C@H:15]([C:18]2[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=2)[CH2:16][CH2:17][N:12]([CH:9]2[CH2:10][CH2:11][N:7]([CH2:6][C:5]3[CH:28]=[CH:29][C:2]([F:1])=[CH:3][CH:4]=3)[C:8]2=[O:27])[CH2:13]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 118207357HCID 118207357, compound

Product 1

HCID 118207434HCID 118207434, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-fluorobenzyl)-3-(trans-3-hydroxy-4-(4-methoxyphenyl)piperidin-1-yl)pyrrolidin-2-one from step B (2.5 g, 6.3 mmol) in 50 mL DCM was added DAST (4.1 mL, 31 mmol) and the reaction was stirred at ambient temperature for 1 h. The reaction was then quenched with a sat.bicarbonate solution (200 mL) and the mixture was extracted with 200 mL of DCM. The organic layer was dried over Na2SO4, filtered, and evaporated under reduced pressure. The residue was purified via silica gel chromatography eluting with 28% ethyl acetate in hexane to give (±)-rel-3-((3S,4S)-3-fluoro-4-(4-methoxyphenyl)piperidin-1-yl)-1-(4-fluorobenzyl)pyrrolidin-2-one (900 mg, 1.6 mmol) as a mixture of four diastereomers. LCMS (method P) RT 0.89 min, m/z 401.2 (M+H+).

Workup

  1. customThe reaction was then quenched with
  2. extractionbicarbonate solution (200 mL) and the mixture was extracted with 200 mL of DCM
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified via silica gel chromatography
  7. washeluting with 28% ethyl acetate in hexane

Sources & evidence

ORD record
ord-dbcb0f65e3414910b1e66d1c7ae5deb7
Source dataset
uspto-grants-2015_12
Patent number
US09221796B2

Reaction notes

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