Triethylamine → (S)-1-Boc-3-methylpiperazine

HRID 22720Notes

Reaction equation

HRID 22720 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C:11](=O)[N:10](C)[CH:9]1[C:15]([CH3:18])(C)C)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[C@H]1CNCCN1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:18][C@@H:15]1[NH:10][CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 546472(R)-1-Boc-2-tert-butyl-3-methyl-4-imidazolidinoneHCID 27342192-Methylpiperazine, (S)-

Product 1

HCID 7023035(S)-1-Boc-3-methylpiperazine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

1-(tert-butoxycarbonyl)-2-tert-butyl-3-methyl-4-imidazolidinone (2 g, 8.3 mmol) (BOC—ON), in chloroform (15 ml), was added to (2S)-2-methylpiperazine (5 g, 50 mmol), a compound of formula (A), in a mixture of triethylamine (1.25 g, 12.5 mmol) and chloroform. The mixture was stirred for about 15 hours and then washed with water, the solvent removed in vacuo. The residue was purified by column chromatography, to give tert-butyl (3S)-3-methylpiperazinecarboxylate, a compound of formula (B).

Workup

  1. washwashed with water
  2. customthe solvent removed in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-182168b7a48648cf91d58092eaab5d2c
Source dataset
uspto-grants-2005_02
Patent number
US06849632B2

Reaction notes

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