Triethylamine → HCID 69156589, compound

HRID 1624303Notes

Reaction equation

HRID 1624303 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:14]O)[CH2:13][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CCN(CC)CC.CS(Cl)(=O)=O.[C:28]1(=[O:38])[NH:32][C:31](=[O:33])[C:30]2=[CH:34][CH:35]=[CH:36][CH:37]=[C:29]12.[K]>C(Cl)Cl.C(OCC)(=O)C.[Cl-].[Na+].O.O>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:14][N:32]2[C:28](=[O:38])[C:29]3[C:30](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:31]2=[O:33])[CH2:12][CH2:13]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 24194345Phthalimide potassium saltHCID 69156419HCID 69156419, compound

Product 1

HCID 69156589HCID 69156589, compoundYield 38%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
80 °C

Procedure

To solution of {1-[2-(tert-butyldimethylsilyloxy)-ethyl]-cyclopropyl}-methanol (0.41 g, 1.78 mmol) in CH2Cl2 (18 mL) was added Et3N (0.50 mL, 3.59 mmol) followed by methanesulfonyl chloride (0.21 mL, 231 mmol). The resultant mixture was stirred at room temperature for 17 hours. The mixture was diluted CH2Cl2 (50 mL), washed with brine (3×20 mL), dried (Na2SO4), and concentrated. The resultant oil was dissolved in DMF (16 mL), treated with potassium phthalimide (0.606 g, 3.27 mmol), and the mixture was heated at 80° C. for 6 hours then cooled to room temperature. The mixture was diluted with ethyl acetate (40 mL), brine (20 mL), and water (10 mL) and the phases were separated. The organic phase was washed with brine (3×10 mL), dried (MgSO4), and concentrated. The crude material was purified by column chromatography on silica gel (20:1 hexanes-ethyl acetate) and provided 0.24 g (38%) of 2-{1-[2-(tert-butyldimethylsilyloxy)-ethyl]-cyclopropylmethyl}-isoindole-1,3-dione as a colorless oil.

Workup

  1. washwashed with brine (3×20 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. dissolutionThe resultant oil was dissolved in DMF (16 mL)
  5. temperaturethen cooled to room temperature
  6. customthe phases were separated
  7. washThe organic phase was washed with brine (3×10 mL)
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated
  10. customThe crude material was purified by column chromatography on silica gel (20:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-b12accbc05434b01b6d1798efb5d48a2
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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