1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate → 1,1-Dimethylethyl (1S,4S)-5-(3-methyl-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

HRID 2098445Notes

Reaction equation

HRID 2098445 reaction equation
[CH3:1][C:2]([CH3:32])([CH3:31])[C@@H:3]([C:15]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][N:20]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[NH:4]C(OCC1C=CC=CC=1)=O>CO.[Pd]>[CH3:1][C:2]([CH3:32])([CH3:31])[C@@H:3]([C:15]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][N:20]2[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[O:16])[NH2:4]

Participants

4

Reactant 1

HCID 672158231,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 582864131,1-Dimethylethyl (1S,4S)-5-(3-methyl-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (1S,4S)-5-(3-methyl-N-{[(phenylmethyl)oxy]carbonyl}-L-valyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (31.6 g, 71 mmol) in MeOH (600 mL) was added Pd/C (12 g). The mixture was stirred for 18 h at room temperature under an atmosphere of H2 (40 psi). The reaction mixture was then filtered and the organic layer was concentrated to yield the crude product. LCMS (m/z): 312.3 (M+H).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-b1d5890961554f29aab268cc2dff4e22
Source dataset
uspto-grants-2013_05
Patent number
US08450484B2

Reaction notes

Loading…