Hydrochloric Acid → HCID 57974048, compound

HRID 1864869Notes

Reaction equation

HRID 1864869 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[NH:14][C:13](=[O:15])[C:12]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.[H-].[Na+].Br[CH2:23][C:24]([O:26]C)=[O:25].[OH-].[Na+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]2[N:14]([CH2:23][C:24]([OH:26])=[O:25])[C:13](=[O:15])[C:12]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 58118717HCID 58118717, compound

Product 1

HCID 57974048HCID 57974048, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (6S)-6-(3,5-difluorophenyl)-3,3-diethylpiperidin-2-one from Step E (850 mg, 3.18 mmol) in THF (15 mL) at ambient temperature was added NaH (178 mg of a 60% dispersion in oil, 4.45 mmol). After 15 min, methyl bromoacetate (0.469 mL, 5.09 mmol) was added and the mixture was stirred for 1 h. Sodium hydroxide (9.54 mL of a 1 M solution, 9.54 mmol) was added and the mixture stirred for an additional 16 h at 50° C. The reaction mixture was poured onto 1 M HCl (30 mL) and extracted with EtOAc (3×30 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo to provide the title compound, which could be used without further purification. MS: m/z=326 (M+1).

Workup

  1. stirringthe mixture stirred for an additional 16 h at 50° C
  2. extractionextracted with EtOAc (3×30 mL)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-313ebd359b3c4bb98b8c39db16c5b3cd
Source dataset
uspto-grants-2009_12
Patent number
US07625901B2

Reaction notes

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