Potassium Carbonate → HCID 70981418, compound

HRID 1475290Notes

Reaction equation

HRID 1475290 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].[CH2:13]([N:20]1[CH2:25][C@H:24]([CH2:26][CH3:27])[NH:23][CH2:22][C@H:21]1[CH3:28])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.C(Cl)(Cl)Cl>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:23]1[CH2:22][C@@H:21]([CH3:28])[N:20]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:25][C@@H:24]1[CH2:26][CH3:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 62576Benzyl bromoacetateHCID 66841931HCID 66841931, compound

Product 1

HCID 70981418HCID 70981418, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6342AcetonitrileSolvent

Procedure

Benzyl bromoacetate (2.6 mL, 16 mmol) was added to a solution of (2R,5S)-1-benzyl-5-ethyl-2-methyl-piperazine (3.5 g, 16 mmol) in acetonitrile (20 mL) containing K2CO3 (2.4 g, 17.6 mmol). The reaction mixture was stirred at ambient temperature overnight. The suspension was diluted with CHCl3 and the solid was filtered off. Filtrate was evaporated in vacuo and the residue was purified by SiO2 chromatography (EtOAc:petrol 4:6) to give ((2S,5R)-4-benzyl-2-ethyl-5-methyl-piperazin-1-yl)-acetic acid benzyl ester (3.4 g) as a pale yellow oil. 1H NMR (CDCl3): 7.46-7.14 (10H, m), 5.18 (2H, d), 4.10 (1H, d), 3.49 (1H, d), 3.32 (1H, d), 3.17 (1H, d), 2.91-2.79 (1H, m), 2.73 (1H, dd), 2.60-2.42 (3H, m), 2.01-1.79 (1H, m), 1.60-1.44 (1H, m), 1.41-1.23 (1H, m), 1.14 (3H, d), 0.77 (3H, t).

Workup

  1. filtrationthe solid was filtered off
  2. customFiltrate was evaporated in vacuo
  3. customthe residue was purified by SiO2 chromatography (EtOAc:petrol 4:6)

Sources & evidence

ORD record
ord-21e9165aff23491ea21737dc8d498cb9
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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