t-Butylammonium fluoride → 4-tert-Butoxycarbonyl-1-(3-chlorophenyl)-5(S)-(2-fluoroethyl)-piperazin-2-one

HRID 342158Notes

Reaction equation

HRID 342158 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15]OS(C)(=O)=O)[CH2:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:10](=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F-:29].C([NH3+])(C)(C)C>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][F:29])[CH2:12][N:11]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)[C:10](=[O:28])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 22941056(S)-4-(tert-butoxycarbonyl)-1-(3-chlorophenyl)-5-[2-(methanesulfonyloxy)ethyl]piperazin-2-one

Product 1

HCID 153910124-tert-Butoxycarbonyl-1-(3-chlorophenyl)-5(S)-(2-fluoroethyl)-piperazin-2-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-tert-Butoxycarbonyl-1-(3-chlorophenyl)-5(S)-(2-methylsulfonyloxyethyl)-piperazin-2-one (0.433 g, 1.00 mmol) and tert-butylammonium fluoride (3.0 mL, 1M in THF) were stirred at room temperature in acetonitrile (5 mL) for 72 h. The reaction was quenched with saturated sodium bicarbonate and extracted with ethyl acetate. The organic extracts were dried, concentrated and purified by column chromatography using 20% ethyl acetate in hexane. The title compound was obtained as a thick oil.

Workup

  1. customThe reaction was quenched with saturated sodium bicarbonate
  2. extractionextracted with ethyl acetate
  3. customThe organic extracts were dried
  4. concentrationconcentrated
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-4251fadc330e4cf293e3348e4a6c2a2a
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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