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

HRID 1873550Notes

Reaction equation

HRID 1873550 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-7e12a3f4e57d40238325cc48a2cf3104
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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