HCID 117697744, compound → HCID 117697930, compound

HRID 1778483Notes

Reaction equation

HRID 1778483 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][O:6][CH:7]1[CH2:14][CH:13]2[N:15](C(OCC3C=CC=CC=3)=O)[CH:9]([CH2:10][O:11][CH2:12]2)[CH2:8]1)[CH3:2]>CCO.[Pd]>[CH:13]12[NH:15][CH:9]([CH2:8][CH:7]([O:6][CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:26])[CH2:14]1)[CH2:10][O:11][CH2:12]2

Participants

4

Reactant 1

HCID 117697744HCID 117697744, compound

Product 1

HCID 117697930HCID 117697930, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of intermediate benzyl 7-(2-ethoxy-2-oxo-ethoxy)-3-oxa-9-azabicyclo[3.3.1]nonane-9-carboxylate (144 mg, 0.40 mmol) in EtOH (10 mL) was added 10% Pd/C (20 mg). The mixture was charged with H2 and being stirred at room temperature for 2 h. The mixture was filtered through a pad of Celite and washed with EtOH. The resulting filtrate was concentrated in vacuo to give compound 46a (83 mg, 91%). LC/MS: calc'd 230 (MH+), exp 230 (MH+); 1H NMR (MeOD, 400 MHz): 4.18 (dd, J=14.0, 6.8 Hz, 2H), 4.13 (s, 2H), 3.74 (m, 1H), 3.68 (m, 4H), 2.98 (m, 2H), 2.27 (m, 2H), 1.77 (m, 2H), 1.27 (t, J=7.2 Hz, 3H).

Workup

  1. additionThe mixture was charged with H2
  2. filtrationThe mixture was filtered through a pad of Celite
  3. washwashed with EtOH
  4. concentrationThe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-e482a55310804dd6a4ffea636b1a6f44
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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