Acetyl chloride → HCID 57526729, compound

HRID 885848Notes

Reaction equation

HRID 885848 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[CH2:17][C@@H:16]([CH3:18])[NH:15][C@@H:14]([CH3:19])[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(Cl)Cl>[C:5]([O:9][C:10]([N:12]1[CH2:17][C@@H:16]([CH3:18])[N:15]([C:1](=[O:3])[CH3:2])[C@@H:14]([CH3:19])[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 10822535tert-butyl (3R,5S)-3,5-dimethylpiperazine-1-carboxylate

Product 1

HCID 57526729HCID 57526729, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.216 ml, 3.04 mmol) was added to a stirred solution of (3S,5R)-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester (500 mg, 2.34 mmol) and TEA (0.49 ml, 3.51 mmol) in DCM (20 ml). The mixture was stirred at room temperature overnight, then the solvent was evaporated and the residue was partitioned between Et2O and 5% citric acid. The organic phase was dried over Na2SO4 and evaporated in vacuo to give 545 mg of (3S,5R)-4-acetyl-3,5-dimethyl-piperazine-1-carboxylic acid tert-butyl ester as a colourless oil.

Workup

  1. customthe solvent was evaporated
  2. customthe residue was partitioned between Et2O and 5% citric acid
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-95badcaa8e0d4ff7b757d8790a0d90db
Source dataset
uspto-grants-2012_08
Patent number
US08242175B2

Reaction notes

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