Benzyl chloroformate → (S)-4-(3-Hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl ester

HRID 655531Notes

Reaction equation

HRID 655531 reaction equation
C(=O)([O-])O.[Na+].[OH:6][CH2:7][CH2:8][CH2:9][N:10]1[CH2:15][CH2:14][NH:13][C@@H:12]([CH3:16])[C:11]1=[O:17].Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>CC(C)=O.O>[CH2:22]([O:21][C:19]([N:13]1[CH2:14][CH2:15][N:10]([CH2:9][CH2:8][CH2:7][OH:6])[C:11](=[O:17])[C@@H:12]1[CH3:16])=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 66999467(S)-1-(3-Hydroxy-propyl)-3-methyl-piperazin-2-one

Product 1

HCID 67079852(S)-4-(3-Hydroxy-propyl)-2-methyl-3-oxo-piperazine-1-carboxylic acid benzyl esterYield 100.6%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

Sodium hydrogencarbonate (976 mg, 11.6 mmol) was added to a solution of (S)-1-(3-hydroxy-propyl)-3-methyl-piperazin-2-one (example 20D; 1.00 g, 5.81 mmol) in acetone (5 mL) and water (5 mL), then a solution of benzyl chloroformate (1.04 g, 5.81 mmol) in acetone (1 mL) was added at 0° C. The reaction mixture was allowed to reach room temperature over 16 h, then partitioned between ethyl acetate and water. The organic layer was dried (MgSO4), filtered, and evaporated to afford the title compound (1.79 g), which was directly used in the next step.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-7fc32ca3815047e88f510454df1a2911
Source dataset
uspto-grants-2011_12
Patent number
US08071586B2

Reaction notes

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