p-Toluenesulfonic acid → HCID 59075103, compound

HRID 712809Notes

Reaction equation

HRID 712809 reaction equation
CC1(C)[N:6]2[C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH2:9][C@@H:5]2[CH2:4][O:3]1.CC1C=CC(S(O)(=O)=O)=CC=1>CO>[OH:3][CH2:4][C@@H:5]1[NH:6][C:7](=[O:12])[C:8]([CH3:11])([CH3:10])[CH2:9]1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 89370059(7aR)-Tetrahydro-3,3,6,6-tetramethyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one

Product 1

HCID 59075103HCID 59075103, compoundYield 123.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred suspension of (R)-3,3,6,6-tetramethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (D35) (714 mg, 3.89 mmol) in MeOH (15 ml), p-TSA (74 mg, 0.39 mmol) was added and the resulting mixture was heated at reflux for 2 hrs. Solvent was evaporated off and the residue was loaded on SPE-SCX cartridge (5 g). The cartridge was washed with MeOH (3 column volume). The methanolic phase was collected and evaporated to afford the title compound (D36) (690 mg)

Workup

  1. additionwas added
  2. temperaturethe resulting mixture was heated
  3. temperatureat reflux for 2 hrs
  4. customSolvent was evaporated off
  5. washThe cartridge was washed with MeOH (3 column volume)
  6. customThe methanolic phase was collected
  7. customevaporated

Sources & evidence

ORD record
ord-8becd33ec58c4b2ea15da42d5be9b3ac
Source dataset
uspto-grants-2015_11
Patent number
US09181279B2

Reaction notes

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