(Diethylamino)sulfur trifluoride → (S)-4-(3-Fluoro-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

HRID 458027Notes

Reaction equation

HRID 458027 reaction equation
CCN(S(F)(F)[F:7])CC.O[CH2:11][CH:12]([CH3:28])[CH2:13][C@@H:14]1[CH2:18][N:17]([C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[C:16](=[O:27])[CH2:15]1>C(Cl)Cl>[F:7][CH2:11][CH:12]([CH3:28])[CH2:13][C@@H:14]1[CH2:18][N:17]([C@H:19]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH3:20])[C:16](=[O:27])[CH2:15]1

Participants

4

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59093973(S)-4-(3-Hydroxy-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-one

Product 1

HCID 59093999(S)-4-(3-Fluoro-2-methyl-propyl)-1-((S)-1-phenyl-ethyl)-pyrrolidin-2-oneYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To DAST (1 g, 6.2 mmol) in CH2Cl2 (20 mL) at −78° C. was added the alcohol 37 in CH2Cl2 (10 mL). After 1 hour at −78° C. the solution was warmed to room temperature. After 7 hours the solution was carefully quenched with a saturated aqueous solution of sodium bicarbonate and the two layers separated. The organic phase was dried (MgSO4) and concentrated. Flash chromatography (90% to 66% hexane/acetone) of the residue gave the product as an oil (600 mg, 37%). MS m/z 264 (M+H, 100%).

Workup

  1. customAfter 7 hours the solution was carefully quenched with a saturated aqueous solution of sodium bicarbonate
  2. customthe two layers separated
  3. dry with materialThe organic phase was dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-89870a33d6234cca9d14e7911848c6e0
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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