Benzyl (S)-4-((1-(tert-butoxycarbonyl)piperidin-3-yl)methyl)piperazine-1-carboxylate → Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylate

HRID 2371133Notes

Reaction equation

HRID 2371133 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[CH2:9]1)=O)(C)(C)C>FC(F)(F)C(O)=O.ClCCl>[NH:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([CH2:14][N:15]2[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:19][CH2:20]2)[CH2:9]1

Participants

4

Reactant 1

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

Product 1

HCID 59846067Benzyl 4-[(3R)-piperidin-3-ylmethyl]piperazine-1-carboxylateYield 106.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Benzyl 4-{[(3S)-1-(tert-butoxycarbonyl)piperidin-3-yl]methyl}piperazine-1-carboxylate (4.46 g) was stirred in a mixture of trifluoroacetic acid (20 ml) and dichloromethane (200 ml) for two hours at room temperature. The reaction mixture was concentrated in vacuo and the resulting oil separated between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate solution (500 ml). The ethyl acetate layer was separated, dried over magnesium sulphate, filtered then concentrated in vacuo to give the title compound (3.6 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting oil separated between ethyl acetate (200 ml) and saturated aqueous sodium bicarbonate solution (500 ml)
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-fb3b3e77ee4741ddb1851e4f17d5d4c4
Source dataset
uspto-grants-2014_04
Patent number
US08710224B2

Reaction notes

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