(R)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate → tert-Butyl (2R)-2-methylpiperazine-1-carboxylate

HRID 2382203Notes

Reaction equation

HRID 2382203 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C@H:10]([CH3:21])[CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:21][C@@H:10]1[CH2:9][NH:8][CH2:13][CH2:12][N:11]1[C:14]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:15]

Participants

5

Reactant 2

HCID 10085634(R)-Tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylateYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 4-benzyl-2-methylpiperazine-1-carboxylate (10 g, 34.5 mmol) in methanol (100 mL) was added Pd/C (1.0 g) and the reaction mixture was subjected to hydrogenolysis under balloon pressure of hydrogen, at room temperature for 8 h. The reaction mixture was filtered through celite bed and the bed was washed with methanol. The filtrate was concentrated under reduced pressure to afford the crude product which was purified by silica gel (100-200 mesh) column chromatography eluting with 5% methanol in chloroform to afford 4.8 g of (R)-tert-butyl 2-methylpiperazine-1-carboxylate.

Workup

  1. filtrationThe reaction mixture was filtered through celite bed
  2. washthe bed was washed with methanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customto afford the crude product which
  5. customwas purified by silica gel (100-200 mesh) column chromatography
  6. washeluting with 5% methanol in chloroform

Sources & evidence

ORD record
ord-c5306722787b4a098d50ae7409338942
Source dataset
uspto-grants-2012_09
Patent number
US08258306B2

Reaction notes

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