Acetic Acid → HCID 70982022, compound

HRID 1475504Notes

Reaction equation

HRID 1475504 reaction equation
C(O)(=O)C.[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[N:15](CC2C=CC=CC=2)[CH2:14][C@H:13]1[CH3:32])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CCO.[Pd]>[C:5]([O:9][C:10]([N:12]1[CH2:17][C@H:16]([CH2:18][N:19]2[CH2:20][CH2:21][O:22][CH2:23][CH2:24]2)[NH:15][CH2:14][C@H:13]1[CH3:32])=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 70981761(2R,5S)-4-Benzyl-2-methyl-5-morpholin-4-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 70982022HCID 70982022, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Acetic acid (30.0 mL) and Pd/C (10%, 6.0 g) were added to a solution of (2R,5S)-4-benzyl-2-methyl-5-morpholin-4-ylmethyl-piperazine-1-carboxylic acid tert-butyl ester (9.0 g, 23.1 mmol) in EtOH (240 mL) and the resulting mixture was hydrogenated at 1 bar for 3 h. The catalyst was removed by filtration and the solvent was removed in vacuo. The residue was dissolved in DCM (150 mL), the organic solution was washed with saturated aqueous NaHCO3 (150 mL), water (150 mL), dried (MgSO4) and evaporated to give the title compound as a colourless gum (6.57 g, 95%). 1H NMR (CDCl3): 4.32-3.90 (1H, m), 3.77-3.64 (5H, m), 3.30 (1H, dd), 3.16-2.82 (2H, m), 2.67 (1H, dd), 2.59-2.49 (2H, m), 2.47-2.30 (2H, m), 2.21 (1H, dd), 2.17-2.07 (2H, m), 1.47 (9H, s), 1.27 (3H, d).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in DCM (150 mL)
  4. washthe organic solution was washed with saturated aqueous NaHCO3 (150 mL), water (150 mL)
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-718165575d1443cc9dcfc4ce682a20a2
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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