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

HRID 515589노트

반응식

HRID 515589 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-1594d4f4673743319c51c9c09d25a714
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09108966B2

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