Hydrochloric Acid → HCID 57659766, compound

HRID 1011603Notes

Reaction equation

HRID 1011603 reaction equation
[CH:1]1([C@H:4]2[C:8](=[O:9])[CH2:7][CH:6]([CH:10]3[CH2:12][CH2:11]3)[N:5]2C(OC(C)(C)C)=O)[CH2:3][CH2:2]1.Cl.CCN(CC)CC.[F:28][C:29]([F:41])([F:40])[C:30]1[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>O1CCOCC1.CN(C1C=CN=CC=1)C>[CH:1]1([C@H:4]2[C:8](=[O:9])[CH2:7][CH:6]([CH:10]3[CH2:11][CH2:12]3)[N:5]2[S:36]([C:33]2[CH:32]=[CH:31][C:30]([C:29]([F:28])([F:40])[F:41])=[CH:35][CH:34]=2)(=[O:38])=[O:37])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27773994-(Trifluoromethyl)benzenesulfonyl chlorideHCID 57659763HCID 57659763, compound

Product 1

HCID 57659766HCID 57659766, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(2S)-tert-Butyl 2,5-dicyclopropyl-3-oxopyrrolidine-1-carboxylate (20) (127 mg, 0.480 mmol) was placed in dioxane (0.5 mL) and treated with 4N HCl in dioxane (2.0 mL). When reaction was done as indicated by TLC monitoring, it was concentrated in vacuo and used without further purification. This material was dissolved in CH2Cl2 (3 mL) and placed under nitrogen. DMAP (12 mg, 0.096 mmol) and Et3N (0.20 mL, 1.44 mmol) were added and the reaction cooled to 0° C. 4-(Trifluoromethyl)benzene-1-sulfonyl chloride (129 mg, 0.528 mmol) was added and the reaction stirred for 16 hr warming from 0° C. to rt. The reaction was concentrated in vacuo and the resulting crude product was purified by column chromatography using EtOAc/hexane gradients to yield (2S)-2,5-dicyclopropyl-1-(4-(trifluoromethyl)phenylsulfonyl)pyrrolidin-3-one (21) (149 mg, 83% over two steps) as a 58:42 mixture of diastereomers. The product was a clear oil that solidified upon standing. MS (m/z) 374.1 (M+H)+; retention time (210 nM)=8.329 and 8.500 min, method [7].

Workup

  1. customWhen reaction
  2. concentrationwas concentrated in vacuo
  3. customused without further purification
  4. dissolutionThis material was dissolved in CH2Cl2 (3 mL)
  5. temperaturewarming from 0° C. to rt
  6. concentrationThe reaction was concentrated in vacuo
  7. customthe resulting crude product was purified by column chromatography

Sources & evidence

ORD record
ord-b56253ae541a498bbeecae48de191bed
Source dataset
uspto-grants-2011_07
Patent number
US07977368B2

Reaction notes

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