2-Methyl-2-butene → HCID 68625771, compound

HRID 1961612Notes

Reaction equation

HRID 1961612 reaction equation
[CH2:1]([C:3]1([CH:16]=[O:17])[CH2:15][CH:6]2[CH2:7][N:8]([C:10]([N:12]([CH3:14])[CH3:13])=[O:11])[CH2:9][CH:5]2[CH2:4]1)[CH3:2].O.O.P([O-])(O)(O)=[O:21].[Na+].Cl([O-])=O.[Na+].CC(=CC)C>O1CCCC1.O>[CH2:1]([C:3]1([C:16]([OH:21])=[O:17])[CH2:15][CH:6]2[CH2:7][N:8]([C:10](=[O:11])[N:12]([CH3:13])[CH3:14])[CH2:9][CH:5]2[CH2:4]1)[CH3:2]

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 72338939HCID 72338939, compound

Product 1

HCID 68625771HCID 68625771, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Ethyl-5-formyl-N,N-dimethyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 19b (0.4 g, 1.68 mmol) was dissolved in the solvent mixture of 18 mL of tetrahydrofuran and 9 mL of water, followed by addition of sodium dihydrogenphosphate dihydrate (787 mg, 5.04 mmol), sodium chlorite (0.454 g, 5.04 mmol) and 2-methyl-2-butene (354 mg, 5.06 mmol) at 0° C. The reaction mixture was reacted at 0° C. for 2 hours under nitrogen atmosphere. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound 5-ethyl-2-dimethylcarbamoyl-hexahydro-cyclopenta[c]pyrrole-5-carboxylic acid 19c (0.426 g, yield 100%) as a yellow solid which was directly used in the next step.

Workup

  1. customThe reaction mixture was reacted at 0° C. for 2 hours under nitrogen atmosphere
  2. extractionThe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eed2e37083094a9c95061dd1bc048375
Source dataset
uspto-grants-2013_04
Patent number
US08415349B2

Reaction notes

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