(3aR,8aS)-5-Nitro-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one → (3aR,8aS)-5-amino-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one

HRID 83978Notes

Reaction equation

HRID 83978 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@@H:9]3[O:13][C:12](=[O:14])[NH:11][C@@H:10]3[C:15]=2[CH:16]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]2[CH2:8][C@@H:9]3[O:13][C:12](=[O:14])[NH:11][C@@H:10]3[C:15]=2[CH:16]=1

Participants

4

Reactant 1

HCID 66981696(3aR,8aS)-5-Nitro-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one

Product 1

HCID 66981691(3aR,8aS)-5-amino-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-oneYield 69.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(3aR,8aS)-5-Nitro-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one (1.3 g, 5.45 mmol) was dissolved in EtOH (50 mL), transferred to par hydrogenation flask. Pd/C (450 mg) transferred to above flask and subjected to hydrogenation at 30 PSI for 2 h. Reaction mixture filtered through Celite and washed the filter cake with EtOH. Filtrate was concentrated and purified by silica gel column chromatography (50-100% EtOAc:hexanes) to provide (3aR,8aS)-5-amino-3,3a,8,8a-tetrahydroindeno[1,2-d]oxazol-2-one (720 mg, 69%) as a white solid. 1H NMR (DMSO-d6): δ 8.23 (s, 1H), 6.90 (d, 1H, J=8.2 Hz), 6.52-4.49 (m, 2H), 5.20 (app t, 1H, J=6.1 and 7.0 Hz), 5.04 (br s, 2H), 4.91 (d, 1H, J=7.0 Hz), 3.13 (dd, 1H, J=6.7 and 17.0 Hz), 2.89 (d, 1H, J=17.0 Hz). LCMS: purity: 99%; MS (m/e): 191 (MH+).

Workup

  1. customtransferred to par hydrogenation flask
  2. customReaction mixture
  3. filtrationfiltered through Celite
  4. washwashed the filter cake with EtOH
  5. concentrationFiltrate was concentrated
  6. custompurified by silica gel column chromatography (50-100% EtOAc:hexanes)

Sources & evidence

ORD record
ord-5605b71c673d47919347decd827ef916
Source dataset
uspto-grants-2014_09
Patent number
US08846908B2

Reaction notes

Loading…