HCID 57891811, compound → HCID 57891803, compound

HRID 1820679Notes

Reaction equation

HRID 1820679 reaction equation
C1(C[N:8]2[CH2:12][C@H:11]3[CH2:13][C@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@H:10]3[O:9]2)C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[NH2:8][CH2:12][C@@H:11]1[C@H:10]([OH:9])[CH2:15][C@@H:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1

Participants

4

Reactant 1

HCID 57891811HCID 57891811, compound

Product 1

HCID 57891803HCID 57891803, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of (±)-1,1-dimethylethyl (3aR,5S,6aR)-2-(phenylmethyl)hexahydro-2H-cyclopenta[d]isoxazole-5-carboxylate (13.0 g, 42.9 mmole) in EtOH (100 mL) in a Parr flask was added Pd(OH)2 (˜400 mg). The reaction contents were shaken under 50 psi of H2 overnight at RT. The reaction contents were filtered through Celite® (MeOH) and concentrated to give the title compound (7.87, 99%) as a white solid: LC-MS (ES) m/e 216 (M+H)+.

Workup

  1. customThe reaction contents
  2. customThe reaction contents
  3. filtrationwere filtered through Celite® (MeOH)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c24dd990cdd4e819aa888530f40e2b4
Source dataset
uspto-grants-2009_10
Patent number
US07605169B2

Reaction notes

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