Lawesson's reagent → 4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidinthione

HRID 635103Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=O)[C@H:10]2[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[S:33])[C@H:10]2[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

4-(S)-(1-Ethoxycarbonylcyclopropyl)-3-(S)-fluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (6.86 g, 21.48 mmol) was dissolved in dry toluene (100 ml). After adding Lawesson's reagent (5.21 g, 12.89 mmol), the mixture was heated at 60° C. for 30 minutes. After allowing the liquid reaction mixture to cool, toluene was evaporated under reduced pressure and the residue was subjected to flash silica gel column chromatography (eluent: n-hexane:ethyl acetate=4:1) to obtain 6.49 g (90.1%) of the title compound as a pale yellow oily substance.

Workup

customthe liquid reaction mixture
temperatureto cool
customtoluene was evaporated under reduced pressure

Sources & evidence

ORD record: ord-b29855ce03bb4fd587ce99c25969dccc
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184388B2

Reaction notes

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