p-Toluenesulfonic acid → (5S)-4-Methyl-4-azaspiro[2.4]heptane-5-methanol

HRID 1969375Notes

Reaction equation

HRID 1969375 reaction equation
[CH3:1][N:2]1[C@H:8]([CH2:9][O:10]C2CCCCO2)[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:1][N:2]1[C@H:8]([CH2:9][OH:10])[CH2:7][CH2:6][C:3]21[CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67296569HCID 67296569, compound

Product 1

HCID 67296668(5S)-4-Methyl-4-azaspiro[2.4]heptane-5-methanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of (5S)-4-methyl-5-((tetrahydro-2H-pyran-2-yloxy)methyl)-4-azaspiro[2.4]heptane (64 mg, 0.284 mmol) in 10 mL of methanol was added 4-methyl-benzenesulfonic acid (97.8 mg, 0.568 mmol, Aldrich). The reaction mixture was stirred at 50° C. overnight, and then concentrated in vacuo. The residue was treated with 10 mL of saturated Na2CO3 aqueous solution, and extracted with dichloromethane (20 mL×3). The combined organic phases were dried over Na2SO4 and concentrated in vacuo to give the desired product as yellow oil (32 mg, 80%).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with 10 mL of saturated Na2CO3 aqueous solution
  3. extractionextracted with dichloromethane (20 mL×3)
  4. dry with materialThe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-47c97b6bf90043d69c81a734be0fa17a
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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