Acetic Acid → 906810-51-3

HRID 251839Notes

Reaction equation

HRID 251839 reaction equation
[C:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:22][CH3:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:24]([OH:27])(=[O:26])[CH3:25].C(Cl)Cl.CCOCC>CO.[Pd]>[C:24]([OH:27])(=[O:26])[CH3:25].[C:1]([N:8]1[CH2:13][C@@H:12]([CH3:14])[NH:11][CH2:10][C@@H:9]1[CH2:22][CH3:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 6344DichloromethaneHCID 59772640HCID 59772640, compound

Product 1

HCID 66841763906810-51-3

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-Boc-2(S)-ethyl-4-benzyl-5(R)-methylpiperazine (A36; 13.6 g, 43 mmol), glacial acetic acid (2.5 mL) and 10% Pd/C (4.5 g) in methanol (150 mL) was shaken under H2 atmosphere (50 psi) for 24 h. The mixture was filtered through Celite® and the filter cake was washed copiously with EtOAc (˜500 mL). The combined filtrates were dried over anhydrous MgSO4, filtlered, and concentrated under reduced pressure to afford a clear colorless oil. Further co-evaporation with CH2Cl2 (200 mL) and Et2O (2×200 mL) gave the desired 1-Boc-2(S)-ethyl-5(R)-methylpiperazine acetic acid salt (A37, 9.7 g) as a viscous oil.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe filter cake was washed copiously with EtOAc (˜500 mL)
  3. dry with materialThe combined filtrates were dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford a clear colorless oil

Sources & evidence

ORD record
ord-b0d73e4dd5984018b32d61a0ac2dd8c3
Source dataset
uspto-grants-2011_01
Patent number
US07868006B2

Reaction notes

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