HCID 71233371、化合物 → HCID 71233145、化合物

HRID 2409924ノート

反応式

HRID 2409924 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][CH:16]1[CH2:21][CH2:20][CH2:19][N:18](C(OCC2C=CC=CC=2)=O)[CH2:17]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.CC(O)=O.[Pd]>[NH:18]1[CH2:19][CH2:20][CH2:21][CH:16]([NH:15][C@@H:10]2[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]2[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:17]1

参加物

5

反応物 1

HCID 71233371HCID 71233371、化合物

生成物 1

HCID 71233145HCID 71233145、化合物収率 86%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

10% Pd/C (0.20 gm, 0.19 mmol) was added to a solution of benzyl 3-((1R,2R)-2-(tert-butoxycarbonylamino)cyclohexylamino)piperidine-1-carboxylate, (1.73 gm, 4.01 mmol) in MeOH (14.6 mL) and AcOH (1.46 mL). A H2 atmosphere was then introduced via balloon. After 1 h the reaction mixture was filtered through Celite. The catalyst was rinsed with MeOH and the filtrate was concentrated. The residue was partitioned between EtOAc and sat. NaHCO3. The aqueous phase was isolated and extracted with EtOAc. All organic phases were combined, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give the product tert-butyl (1R,2R)-2-(piperidin-3-ylamino)cyclohexylcarbamate (1.02 gm, 3.43 mmol, 86% yield) as a white foam. Anal. Calcd. for C16H31N3O2 m/z 297.2, found: 298.2 (M+H)+. Crude product was used without purification.

後処理

  1. additionA H2 atmosphere was then introduced via balloon
  2. filtrationAfter 1 h the reaction mixture was filtered through Celite
  3. washThe catalyst was rinsed with MeOH
  4. concentrationthe filtrate was concentrated
  5. customThe residue was partitioned between EtOAc and sat. NaHCO3
  6. customThe aqueous phase was isolated
  7. extractionextracted with EtOAc
  8. washwashed with saturated aqueous NaCl
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated

出典と根拠

ORDレコード
ord-eda928b29deb47ffa4c8115968523ec6
出典データセット
uspto-grants-2014_08
特許番号
US08815909B2

反応ノート

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