Pyrrolidine → 1-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-pyrrolidine

HRID 1468182Notes

Reaction equation

HRID 1468182 reaction equation
[CH2:1]1[O:11][C:4]2([CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]2)[O:3][CH2:2]1.[NH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1>C1CCCCC1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:3]1[C:4]2([CH2:9][CH2:8][C:7]([N:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)=[CH:6][CH2:5]2)[O:11][CH2:1][CH2:2]1

Participants

5

Reactant 2

HCID 31268PyrrolidineHCID 5674151,4-Dioxaspiro[4.5]decan-8-one

Product 1

HCID 100818201-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-pyrrolidineYield 30.2%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 8078CyclohexaneSolvent

Procedure

Reflux a solution of 1,4-cyclohexanedione mono-ethylene ketal (10.4 g, 66.5 mmol) and pyrrolidine (4.96 g, 69.8 mmol) and p-toluenesulfonic acid monohydrate (0.13 g, 0.66 mmol) in 50 mL cyclohexane overnight with a Dean-Stark trap and drying tube. Filter the mixture, wash with Et2O and concentrate the brown filtrate to afford 4.20 g of 1-(1,4-dioxa-spiro[4.5]dec-7-en-8-yl)-pyrrolidine as brown oil

Workup

  1. customdrying tube
  2. filtrationFilter the mixture
  3. washwash with Et2O
  4. concentrationconcentrate the brown filtrate

Sources & evidence

ORD record
ord-e31817537cf44e3aac29ce3231017574
Source dataset
uspto-grants-2015_04
Patent number
US09000154B2

Reaction notes

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