Benzyl (S)-4-((1-(tert-butoxycarbonyl)piperidin-3-yl)methyl)piperazine-1-carboxylate → tert-butyl (3S)-3-(piperazin-1-ylmethyl)piperidine-1-carboxylate

HRID 603214Notes

Reaction equation

HRID 603214 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][N:15]2[CH2:20][CH2:19][N:18](C(OCC3C=CC=CC=3)=O)[CH2:17][CH2:16]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO>[N:15]1([CH2:14][C@@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1

Participants

3

Reactant 1

HCID 59846076Benzyl (S)-4-((1-(tert-butoxycarbonyl)piperidin-3-yl)methyl)piperazine-1-carboxylate

Product 1

HCID 24886660tert-butyl (3S)-3-(piperazin-1-ylmethyl)piperidine-1-carboxylateYield 99.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Benzyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]methyl}piperazine-1-carboxylate (5.0 g, 12.4 mmol) was dissolved in methanol (50 ml) in a three-necked flask. The air was removed under reduced pressure and replaced with argon before the addition of 10% Pd/C (1.24 g). A balloon of hydrogen was then added and the reaction stirred at room temperature for 18 h. The hydrogen was evacuated and replaced with argon. The catalyst was then filtered and the solvent removed under reduced pressure to afford the desired product as a white foam (3.5 g). The compound was used without further purification.

Workup

  1. customThe air was removed under reduced pressure
  2. additionreplaced with argon before the addition of 10% Pd/C (1.24 g)
  3. additionA balloon of hydrogen was then added
  4. customThe hydrogen was evacuated
  5. filtrationThe catalyst was then filtered
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8d385fc8785b41149a23554b75ab10a3
Source dataset
uspto-grants-2011_03
Patent number
US07906645B2

Reaction notes

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