Methanol → 6-Benzyl-2-oxa-6-azaspiro[3.4]octan-8-amine

HRID 539982Notes

Reaction equation

HRID 539982 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]([N+:16]([O-])=O)[C:10]2([CH2:13][O:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[NH4+].CO>[Fe].O>[CH2:1]([N:8]1[CH2:15][CH:14]([NH2:16])[C:10]2([CH2:13][O:12][CH2:11]2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 712547596-Benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octane

Product 1

HCID 712545836-Benzyl-2-oxa-6-azaspiro[3.4]octan-8-amine

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The mixture of 6-benzyl-8-nitro-2-oxa-6-aza-spiro[3.4]octane (2 g, 8.1 mmol), iron powder (2.3 g, 40.5 mmol), ammonium chloride (4.3 g, 81 mmol), methanol (40 mL) and 8 mL of water was heated with stirring for 2 hours at 80° C. The reaction mixture was filtered by a pad of celite. The filtrate was concentrated under reduced pressure, and the residue was used for next step without further purification.

Workup

  1. temperaturewas heated
  2. filtrationThe reaction mixture was filtered by a pad of celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was used for next step without further purification

Sources & evidence

ORD record
ord-b79e12d3f2d847fa9d2aefa188457128
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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