Trifluoroacetic acid → Ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate

HRID 1427549Notes

Reaction equation

HRID 1427549 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:15][NH:16][C@H:17]1[CH2:22][N:21](C(OC(C)(C)C)=O)[C@H:20]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:19][CH2:18]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(Cl)Cl>[CH2:8]([O:15][NH:16][C@H:17]1[CH2:22][NH:21][C@H:20]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:19][CH2:18]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86700665(2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate

Product 1

HCID 86675005Ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (600 mL) was added to a solution of (2S,5R)-1-tert-butyl 2-ethyl 5-((benzyloxy)amino)piperidine-1,2-dicarboxylate (263 g, 0.7 mol) in DCM (600 mL) at 20° C. The mixture was stirred at rt overnight and then concentrated in vacuum. The crude product was adjusted to pH 10 with sat. NaHCO3 solution, and then extracted with DCM three times. The combined organic layer was concentrated in vacuum and purified by silica gel column chromatography (20:1 DCM/MeOH) to afford (2S,5R)-ethyl 5-((benzyloxy)amino)piperidine-2-carboxylate (184.9 g, 95%) as a yellow oil.

Workup

  1. concentrationconcentrated in vacuum
  2. extractionextracted with DCM three times
  3. concentrationThe combined organic layer was concentrated in vacuum
  4. custompurified by silica gel column chromatography (20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-202878abd591408ca899188e9ee7d3f2
Source dataset
uspto-grants-2015_01
Patent number
US08933232B2

Reaction notes

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