HCID 71233371, compound → HCID 71233145, compound

HRID 2409924Notes

Reaction equation

HRID 2409924 reaction equation
[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

Participants

5

Reactant 1

HCID 71233371HCID 71233371, compound

Product 1

HCID 71233145HCID 71233145, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-eda928b29deb47ffa4c8115968523ec6
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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