2-Methyl-2-butene → HCID 68626053, compound

HRID 1873542Notes

Reaction equation

HRID 1873542 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([N:5]1[CH2:9][CH:8]2[CH2:10][C:11]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)([CH:13]=[O:14])[CH2:12][CH:7]2[CH2:6]1)=[O:4].O.O.P([O-])(O)(O)=[O:24].[Na+].Cl([O-])=O.[Na+].CC(=CC)C>O1CCCC1.O>[CH:15]1([C:11]2([C:13]([OH:24])=[O:14])[CH2:12][CH:7]3[CH2:6][N:5]([C:3](=[O:4])[N:2]([CH3:20])[CH3:1])[CH2:9][CH:8]3[CH2:10]2)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, DihydrateHCID 72338932HCID 72338932, compound

Product 1

HCID 68626053HCID 68626053, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

5-Cyclopentyl-5-formyl-hexahydro-cyclopenta[c]pyrrole-2-carboxylic acid dimethylamide 16b (0.266 g, 0.955 mmol) was dissolved in a solvent mixture of 20 mL of tetrahydrofuran and 10 mL of water. Then sodium dihydrogenphosphate dihydrate (0.448 g, 2.87 mmol), sodium chlorite (0.26 g, 2.87 mmol) and 2-methyl-2-butene (0.24 mL, 2.88 mmol) were added at 0° C. The reaction mixture was stirred at 0° C. for 2 hours. The reaction was monitored by TLC until the disappearance of the starting materials. The mixture was concentrated to remove tetrahydrofuran and extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound 5-cyclopentyl-2-dimethylcarbamoyl-octahydro-cyclopenta[c]pyrrole-5-carboxylic acid 16c (0.28 g, yield 99.6%) as a yellow solid.

Workup

  1. concentrationThe mixture was concentrated
  2. customto remove tetrahydrofuran
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c7f5a1c2f6f4938968999081fa70d7c
Source dataset
uspto-grants-2012_11
Patent number
US08304411B2

Reaction notes

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