Triethylamine → HCID 20800560, compound

HRID 1454278Notes

Reaction equation

HRID 1454278 reaction equation
[OH:1][CH2:2][CH:3]([N:10]1[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:19])[CH:16]=2)[C:11]1=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:19][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:20])[N:10]([CH:3]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[CH2:2][O:1][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:18]2

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22393547HCID 22393547, compound

Product 1

HCID 20800560HCID 20800560, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(2-Hydroxy-1-phenyl-ethyl)-5-methyl-2,3-dihydro-isoindol-1-one (4.72 g, 17.66 mmol) and triethylamine (5.36 g, 53.97 mmol, 7.38 mL) were taken up in anhydrous DCM (50 mL), under argon and cooled to 0EC. Methanesulfonyl chloride (2.22 g, 19.43 mmol, 1.5 mL) was added to the reaction over 10 min. The reaction was stirred for 1 h at 0EC then allowed to slowly warm to room temp and stirred for 4 h. The reaction was slowly poured into saturated sodium bicarbonate and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with 1N HCl, water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was used in the next step without further purification. Yield 5.61 g. 1H NMR (CDCl3, 300 MHz): δ 2.44 (s, 3H), 3.01 (s, 3H), 4.15 (d, J=16 Hz, 1H), 4.43 (d, J=17 Hz, 1H), 4.77 (dd, J=5, 11 Hz, 1H), 5.03 (dd, J=9, 11 Hz, 1H), 5.76 (dd, J=5, 9 Hz, 1H), 7.20-7.38 (, 7H), 7.76 (d, J=8, 1H).

Workup

  1. temperaturecooled to 0EC
  2. stirringstirred for 4 h
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with 1N HCl, water, brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was used in the next step without further purification

Sources & evidence

ORD record
ord-26b7f55cdbed4bc29ffed3cb71d85062
Source dataset
uspto-grants-2009_01
Patent number
US07479495B2

Reaction notes

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