Hydrochloric Acid → 3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)aniline

HRID 1410066Notes

Reaction equation

HRID 1410066 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[CH2:16][C@H:15]3[O:17][C@H:12]([CH2:13][CH2:14]3)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C([O-])(O)=O.[Na+]>O1CCOCC1.O.[Zn]>[C@@H:12]12[O:17][C@@H:15]([CH2:14][CH2:13]1)[CH2:16][N:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])[CH2:11]2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 68379304(1R,5S)-3-(3-nitrophenyl)-8-oxa-3-azabicyclo[3.2.1]octane

Product 1

HCID 683792583-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)anilineYield 88%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of (1R,5S)-3-(3-nitrophenyl)-8-oxa-3-azabicyclo[3.2.1]octane (0.08 g, 0.341 mmol) and Zn (0.223 g, 3.41 mmol) in dioxane (10 mL) and H2O (2 mL) was added dropwise conc. HCl (0.34 mL, 3.41 mmol) at 25° C. for 2 h. It was adjusted to pH=8 by the addition of solid NaHCO3. It was filtered and the filtration was extracted with ethyl acetate (2×10 mL) and the extraction was concentrated to dryness. The residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with ethyl acetate:petroleum ether=1:2) to afford 3-((1R,5S)-8-oxa-3-azabicyclo[3.2.1]octan-3-yl)aniline (0.061 g, 88%) as a yellow oil. LC-MS: 205 [M+H]+, tR=1.09 min.

Workup

  1. filtrationIt was filtered
  2. filtrationthe filtration
  3. extractionwas extracted with ethyl acetate (2×10 mL)
  4. extractionthe extraction
  5. concentrationwas concentrated to dryness
  6. customThe residue was purified by column chromatography (silica gel, 200˜300 mesh, eluting with ethyl acetate:petroleum ether=1:2)

Sources & evidence

ORD record
ord-f5ecb04d00014e4c938275ce2937a2ee
Source dataset
uspto-grants-2014_12
Patent number
US08921383B2

Reaction notes

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