Methanol → HCID 22025447, compound

HRID 733282Notes

Reaction equation

HRID 733282 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C:10](=[O:14])[N:9]([CH2:15][C:16]([F:19])([F:18])[F:17])[C:8]2=[O:20])(=[O:4])=[O:3].CO>O>[OH:20][CH:8]1[C:7]2[C:11](=[CH:12][CH:13]=[C:5]([S:2]([CH3:1])(=[O:3])=[O:4])[CH:6]=2)[C:10](=[O:14])[N:9]1[CH2:15][C:16]([F:19])([F:17])[F:18]

Participants

4

Reactant 2

HCID 887MethanolHCID 22025429HCID 22025429, compound

Product 1

HCID 22025447HCID 22025447, compoundYield 40.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.4 g of 5-methanesulfonyl-2-(2,2,2-trifluoro-ethyl)-isoindole-1,3-dione were dissolved using 240 ml of MeOH. 0.63 g of KBH4 were then added in small portions at ambient temperature. The reaction mixture was stirred for 20 h at ambient temperature and subsequently poured into 1 l of water at 0° C. The aqueous layer was then extracted three times using 300 ml of CH2Cl2 each time. Then, the aqueous layer was extracted four times using 300 ml of EA each time. Each organic layer was dried separately over Na2SO4. The solvents were removed in vacuo. The EA layer yielded 1.4 g pure product as a pale yellow oil. The CH2Cl2 layer was chromatographed on silica gel using EA/HEP 1:2 yielding another 1.5 g of product (Rf(EA/HEP 1:2)=0.035; MS (DCI): 310 (M+1)+)

Workup

  1. extractionThe aqueous layer was then extracted three times
  2. extractionThen, the aqueous layer was extracted four times
  3. dry with materialEach organic layer was dried separately over Na2SO4
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-6e93088e21ea43e0bfdb72e3cf81cf36
Source dataset
uspto-grants-2009_09
Patent number
US07589117B2

Reaction notes

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