Sodium Hydroxide → 3-(Phenylmethyl)-7-oxa-3-azabicyclo[4.1.0]heptane

HRID 1505648Notes

Reaction equation

HRID 1505648 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]=[CH:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C(=O)N(Br)C(=[O:17])C1.[OH-].[Na+]>O.FC(F)(F)C(O)=O>[CH2:1]([N:8]1[CH2:9][CH2:10][CH:11]2[CH:12]([O:17]2)[CH2:13]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 64215731-BENZYL-1,2,3,6-TETRAHYDROPYRIDINE

Product 1

HCID 64214963-(Phenylmethyl)-7-oxa-3-azabicyclo[4.1.0]heptaneYield 3,337.2%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 962WaterSolvent

Procedure

3.36 g of 1-benzyl-1,2,3,6-tetrahydropyridine (0.19 mmol) was dissolved in 35 mL of water containing 1.5 mL of trifluoroacetic acid (0.2 mmol). To that solution 5.87 g of NBS was added in small portions. After 4 hs reaction mixture was transferred to 50 mL of 20% NaOH solution and stirred overnight. On the morning reaction mixture was extracted with dichloromethane and combined organic fractions were dried over sodium sulfate and concentrated. The residue was purified on silica gel column using hexane-ethyl acetate 3:1 as eluent. Evaporation of solvent produced 1.2 g of 3-benzyl-7-oxa-3-azabicyclo[4.1.0]heptane as colorless oil.

Workup

  1. customAfter 4 hs reaction mixture
  2. customOn the morning reaction mixture
  3. extractionwas extracted with dichloromethane
  4. dry with materialwere dried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel column
  7. customEvaporation of solvent

Sources & evidence

ORD record
ord-079f2d5f617c48c29b82e2586a37ac3c
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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