Hydrochloric Acid → (S)-3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-one

HRID 407884Notes

Reaction equation

HRID 407884 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[C:26]([F:33])=[CH:25][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH:11]2[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]2)[C:6]1=[O:24].Cl.CC(O)C>CO>[F:1][C:2]1[CH:28]=[C:27]([S:29]([CH3:32])(=[O:31])=[O:30])[C:26]([F:33])=[CH:25][C:3]=1[O:4][C@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:6]1=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 66803465HCID 66803465, compound

Product 1

HCID 66802663(S)-3-(2,5-Difluoro-4-(methylsulfonyl)phenoxy)-1,4'-bipiperidin-2-oneYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-tert-butyl 3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-2-oxo-1,4′-bipiperidine-1′-carboxylate (370 mg, 0.757 mmol) in methanol (5 mL) was added, 5 M HCl in IPA (1.51 mL, 7.57 mmol) and the mixture was stirred at ambient temperature for 6 hours and concentrated in vacuo. The residue was stirred in 1M NaOH (20 mL) and DCM (25 mL). The organic layers were combined, dried (Na2SO4), filtered and concentrated in vacuo to give (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-[1,4′-bipiperidin]-2-one as light brown foam (282 mg, 0.726 mmol, 96% yield). Mass spectrum (apci) m/z=389.1 (M+H).

Workup

  1. concentrationconcentrated in vacuo
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-906cad8304404e99a8f11a8d96f6dc73
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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