HCID 86643339, compound → HCID 11160773, compound

HRID 1948307Notes

Reaction equation

HRID 1948307 reaction equation
C(OC([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C@@H:13]1[O:23][CH3:24])=O)C1C=CC=CC=1>CO.Cl.[Pd].C>[NH2:11][C@@H:12]1[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:14][C@@H:13]1[O:23][CH3:24]

Participants

5

Reactant 1

HCID 86643339HCID 86643339, compound2×

Product 1

HCID 11160773HCID 11160773, compoundYield 117%

Reagents, catalysts & solvents 3

HCID 14818447PalladiumcarbonCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

ethyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidine-1-carboxylate (Intermediate 24; 3.98 g) was dissolved in MeOH (100 ml) and 1N HCl (50 ml). 10% Pd-charcoal (600 mg) was added, degassed and hydrogenolysed under an atmosphere of H2 gas at room temperature for 3 h. The catalyst was filtered through a bed of celite, concentrated in vacuo and lyophilized giving the title compound (2.8 g). MS (ES) MH+: 202 for C9H18N2O3.

Workup

  1. customdegassed
  2. filtrationThe catalyst was filtered through a bed of celite,
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-569bb0d5fadf496496e558aff8d27dc9
Source dataset
uspto-grants-2013_03
Patent number
US08399489B2

Reaction notes

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