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

HRID 870816ノート

反応式

HRID 870816 の反応式
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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-26fc4dfaa61643c7bbc5efb8fb9cce51
出典データセット
uspto-grants-2015_03
特許番号
US08969570B2

反応ノート

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