Trifluoroacetic acid → 2-(((Tert-butyldimethylsilyl)oxy)methyl)-1-(oxetan-3-yl)piperazine

HRID 921688Notes

Reaction equation

HRID 921688 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[N:15]([CH:16]2[CH2:19][O:18][CH2:17]2)[CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[Si:1]([O:8][CH2:9][CH:10]1[CH2:11][NH:12][CH2:13][CH2:14][N:15]1[CH:16]1[CH2:19][O:18][CH2:17]1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86708558Tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-4-(oxetan-3-yl)piperazine-1-carboxylate

Product 1

HCID 867085572-(((Tert-butyldimethylsilyl)oxy)methyl)-1-(oxetan-3-yl)piperazineYield 97.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl 3-(((tert-butyldimethylsilyl)oxy)methyl)-4-(oxetan-3-yl)piperazine-1-carboxylate (714 mg, 1.847 mmol) was taken up in DCM (8 mL) and TFA (2.85 mL, 36.9 mmol) was added. The reaction was stirred at room temperature for 30 min. The solvent was removed in vacuo and the material was dissolved in MeOH. The solution was loaded onto an SCX column (3×5 g, benzenesulfonic acid sorbent) and the columns were flushed with MeOH, then 7N NH3/MeOH to release the product. (+/−)2-(((tert-butyldimethylsilyl)oxy)methyl)-1-(oxetan-3-yl)piperazine (517 mg) was obtained as a yellow oil.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe material was dissolved in MeOH
  3. customthe columns were flushed with MeOH

Sources & evidence

ORD record
ord-aa5fd7c611284642a7933ec2f53d6b14
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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