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

HRID 1424511Notes

Reaction equation

HRID 1424511 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 under reduced pressure. The crude product was adjusted to pH 10 with sat. NaHCO3 solution then extracted with DCM (3×). The combined organic layer was concentrated under reduced pressure 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 under reduced pressure
  2. extractionthen extracted with DCM (3×)
  3. concentrationThe combined organic layer was concentrated under reduced pressure
  4. custompurified by silica gel column chromatography (20:1 DCM/MeOH)

Sources & evidence

ORD record
ord-db8478bb2b394a8e97bee404c886eed2
Source dataset
uspto-grants-2015_01
Patent number
US08927724B2

Reaction notes

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