HCID 86726845, compound → HCID 86726798, compound

HRID 1499572Notes

Reaction equation

HRID 1499572 reaction equation
C(OC([N:11]1[CH2:16][C@H:15]([CH3:17])[C@:14]([OH:19])([CH3:18])[C@H:13]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12]1)=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[C:24]([O:23][C:21](=[O:22])[NH:20][C@H:13]1[C:14]([OH:19])([CH3:18])[C@@H:15]([CH3:17])[CH2:16][NH:11][CH2:12]1)([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 86726845HCID 86726845, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86726798HCID 86726798, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Benzyl-(3R,4R,5S)-3-[(tert-butoxycarbonyl)amino]-4-hydroxy-4,5-dimethylpiperidine-1-carboxylate (414 mg, 1.09 mmol) in a vial was dissolved in MeOH (10 mL) and 10% palladium on carbon (100 mg) was added. The vial was closed with septum and connected to a balloon filled with hydrogen. The reaction mixture was stirred at room temperature overnight. The solution was filtered to remove the palladium on carbon and solvent was evaporated under reduced pressure to give the sub-title compound as a colorless oil (245 mg, 92%), which was used in the next step without further purification. LCMS calc. for C12H25N2O3 (M+H)+ m/z=245.2. found 245.1.

Workup

  1. customThe vial was closed with septum
  2. filtrationThe solution was filtered
  3. customto remove the palladium on carbon and solvent
  4. customwas evaporated under reduced pressure

Sources & evidence

ORD record
ord-f6bf31048b60438aa4f488390e2287d3
Source dataset
uspto-grants-2015_12
Patent number
US09200004B2

Reaction notes

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