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

HRID 1406849ノート

反応式

HRID 1406849 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 stiffed 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-12ec75ef52904e9689fb59ff7d9d368e
出典データセット
uspto-grants-2014_12
特許番号
US08916709B2

反応ノート

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