(3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate → 1-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate

HRID 365441Notes

Reaction equation

HRID 365441 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([NH:14]C(OCC2C=CC=CC=2)=O)[CH2:11][C@H:10]([C:25]([O:27][CH3:28])=[O:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([NH2:14])[CH2:11][C@H:10]([C:25]([O:27][CH3:28])=[O:26])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 70274467(3S,5R)-1-tert-Butyl 3-Methyl 5-(((Benzyloxy)carbonyl)amino)piperidine-1,3-dicarboxylate

Product 1

HCID 702740551-tert-Butyl 3-methyl (3S,5R)-5-aminopiperidine-1,3-dicarboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

1-(t-Butoxycarbonyl)-cis-3-methoxycarbonyl-5-(benzyloxycarbonyl)amino piperidine (2.55 g, 6.51 mmol) was dissolved in EtOAc (75 mL), treated with Pd/C (510 mg) and shaken on a Parr apparatus at 45 psi overnight. The reaction mixture was filtered through celite, concentrated, and chromatographed (silica gel, 2% MeOH/CH2Cl2 with NH4OH) to give the title compound.

Workup

  1. filtrationThe reaction mixture was filtered through celite,
  2. concentrationconcentrated
  3. customchromatographed (silica gel, 2% MeOH/CH2Cl2 with NH4OH)

Sources & evidence

ORD record
ord-0149566554324892b98fb0a53cb01d38
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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