Diethanolamine → HCID 68843502, compound

HRID 1725339Notes

Reaction equation

HRID 1725339 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([F:17])[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1)=[O:4].B(Cl)([C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1)[C@@H]1[C@@H](C)[C@@H]2C(C)(C)[C@@H](C2)C1.N(CCO)CCO>C1(C)C=CC=CC=1>[Br:1][CH2:2][C@@H:3]([C:5]1[C:14]2[C:9](=[C:10]([F:17])[CH:11]=[C:12]([O:15][CH3:16])[CH:13]=2)[N:8]=[CH:7][CH:6]=1)[OH:4]

Participants

5

Reactant 3

HCID 8113DiethanolamineHCID 13515837Chlorobis(2,6,6-trimethylbicyclo(3.1.1)heptan-3-yl)boraneHCID 22281740HCID 22281740, compound

Product 1

HCID 68843502HCID 68843502, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

8.0 g (26.8 mmol) of 2-Bromo-1-(8-fluoro-6-methoxy-quinolin-4-yl)-ethanone was dissolved in 200 mL of toluene. 17.2 g (53.6 mmol) of (+)-DIP-chloride was added and the contents were allowed to stir at rt overnight (16 hrs). 8 mL (80.4 mmol) of diethanolamine was added and the contents were allowed to stir at rt for 3 hrs. The contents were filtered and the solids washed; first with hot toluene, then with ethyl acetate until the washings no longer had UV activity. The crude material was preadsorbed onto silica gel and purified by flash chromatography using 2:1 hexanes/ethyl acetate and going to 100% ethyl acetate afforded 7.95 g (98%) of the product. 1H NMR (DMSO, 400 MHz) 8.81 (d, 1H), 7.71 (d, 1H), 7.39 (d, 1H), 7.30 (s, 1H), 6.28 (d, 1H), 5.75 (m, H), 4.00 (s, 3H), 3.97 (dd, 1H), 3.91 (dd, 1H). LCMS (M+H)+ 300. Enantiomeric excess was determined by chiral HPLC to be ≧94%.

Workup

  1. stirringto stir at rt for 3 hrs
  2. filtrationThe contents were filtered
  3. washthe solids washed
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-70524f8c8e7a40009ef47ef605237384
Source dataset
uspto-grants-2009_02
Patent number
US07491714B2

Reaction notes

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