Acetic Acid → 4-Benzyl-5-methoxymethyl-5-methyl-piperazin-2-one

HRID 334082Notes

Reaction equation

HRID 334082 reaction equation
C([O:3][C:4](=O)[CH2:5][N:6]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:7]([C:12]#[N:13])([CH3:11])[CH2:8][O:9][CH3:10])C.[BH4-].[Na+].C(O)(=O)C>CO.O.[Co](Cl)Cl>[CH2:14]([N:6]1[C:7]([CH2:8][O:9][CH3:10])([CH3:11])[CH2:12][NH:13][C:4](=[O:3])[CH2:5]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 86688304[Benzyl-(1-cyano-2-methoxy-1-methyl-ethyl)-amino]-acetic acid ethyl ester

Product 1

HCID 866883054-Benzyl-5-methoxymethyl-5-methyl-piperazin-2-one

Reagents, catalysts & solvents 3

HCID 24288Cobalt(II) chlorideCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 545 mg (1.78 mmol) [benzyl-(1-cyano-2-methoxy-1-methyl-ethyl)-amino]-acetic acid ethyl ester in 10 mL MeOH was added 460 mg (3.57 mmol) cobalt(II) chloride. The mixture was cooled with ice and 270 mg (7.13 mmol) sodium borohydride was added. The resulting mixture was stirred at RT for 1 h. The reaction mixture was diluted with a small amount of water, acidified with acetic acid and stirred for 30 min. The organic solvent was removed by distillation; the residue was alkalized with 4 N aqueous NaOH solution and filtered through Celite. The solvent was extracted with EtOAc. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo.

Workup

  1. additionwas added
  2. stirringstirred for 30 min
  3. customThe organic solvent was removed by distillation
  4. filtrationfiltered through Celite
  5. extractionThe solvent was extracted with EtOAc
  6. dry with materialThe combined organic phases were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-615a10d57fff46df904498d502d97c74
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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