Hydrochloric Acid → HCID 66841931, compound
Reaction equation
B.[CH2:2]([N:9]1[C@H:14]([CH3:15])[C:13](=O)[NH:12][C@@H:11]([CH2:17][CH3:18])[C:10]1=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CO.Cl>C1COCC1>[CH2:2]([N:9]1[CH2:10][C@H:11]([CH2:17][CH3:18])[NH:12][CH2:13][C@H:14]1[CH3:15])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
A solution of borane in THF (1 M, 197 mL) was slowly added to (3S,6R)-1-benzyl-3-ethyl-6-methyl-piperazine-2,5-dione (4.9 g, 19.7 mmol) over 15 min under nitrogen. The reaction mixture was then stirred at 70° C. for 72 h. The resulting solution was cooled to 0° C. and MeOH (60 mL) and 5 M hydrochloric acid (16 mL) were slowly added, then the solution was heated at 70° C. with stirring for 2 h. The solvent was removed in vacuo, and the residue was partitioned between water and Et2O. 1 M aqueous NaOH was added to give pH 12 and the product was extracted with EtOAc (3×). The organic phase was dried (MgSO4), filtered and concentrated to give (2R,5S)-1-benzyl-5-ethyl-2-methyl-piperazine (3.5 g) as a yellow liquid. MS: [M+H]+=219.
Workup
- temperatureThe resulting solution was cooled to 0° C.
- temperaturethe solution was heated at 70° C.
- stirringwith stirring for 2 h
- customThe solvent was removed in vacuo
- customthe residue was partitioned between water and Et2O
- addition1 M aqueous NaOH was added
- customto give pH 12
- extractionthe product was extracted with EtOAc (3×)
- dry with materialThe organic phase was dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-3294a9ff6b854706b0036919d35b4e79
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018214B2
Reaction notes
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