Sulfuric Acid → 3-Benzyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acid

HRID 484204Notes

Reaction equation

HRID 484204 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]#N)([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-:16].[Ba+2].[OH-:18].S(=O)(=O)(O)O>O>[CH2:1]([N:8]1[CH2:13][CH:12]2[C:10]([C:14]([OH:18])=[O:16])([CH2:11]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6093286Barium hydroxideHCID 121996873-Benzyl-3-azabicyclo[3.1.0]hexane-1-carbonitrile

Product 1

HCID 157134313-Benzyl-3-azabicyclo[3.1.0]hexane-1-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-benzyl-1-cyano-3-azabicyclo[3.1.0]hexane (2.77 g, 14.0 mmol) and barium hydroxide (4.47 g, 14.2 mmol) in water (100 ml) was heated to reflux for 18 hours. The reaction was then cooled and brought to neutral pH with sulfuric acid. The thick white mixture was filtered and washed twice with ethanol and twice with water. The filtrate was concentrated in vacuo, and the residue mixed with hot ethanol and filtered again. The filtrate was concentrated to provide the title product (2.91 g, 13.4 mmol, 96% yield). 1H NMR (D2O): 7.50 (bs, 5H), 4.36 (s, 2H), 3.9 (bs, 1H), 3.6 (m, 1H), 3.5 (bm, 2H), 2.14 (bs, 1H), 1.53 (bs, 1H), 1.09 (bs, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction was then cooled
  4. filtrationThe thick white mixture was filtered
  5. washwashed twice with ethanol and twice with water
  6. concentrationThe filtrate was concentrated in vacuo
  7. additionthe residue mixed with hot ethanol
  8. filtrationfiltered again
  9. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-96bd7cec4e6949be91785019c4a9ebb2
Source dataset
uspto-grants-1993_07
Patent number
US05229396

Reaction notes

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