Acetic Acid → HCID 67440655, compound

HRID 1664334Notes

Reaction equation

HRID 1664334 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]3[B:15]([OH:16])[O:14][CH2:13][C:12]=3[CH:17]=2)=[C:5]([CH:20]=O)[CH:4]=1)#[N:2].[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(O)(=O)C.C([BH3-])#N>CO.O>[OH:16][B:15]1[C:11]2[CH:10]=[CH:9][C:8]([O:7][C:6]3[CH:18]=[CH:19][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[CH2:20][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][C:12]=2[CH2:13][O:14]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 498716Cyano-borohydrideHCID 86636417HCID 86636417, compound

Product 1

HCID 67440655HCID 67440655, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of 5-(4-Cyano-2-formylphenoxy)-1,3-dihydro-1-hydroxy-2,1-benzoxaborole (D23) (0.400 g, 1.43 mmol), morpholine (0.375 mL, 4.29 mmol), and acetic acid (0.246 mL, 4.29 mmol) in methanol (10 mL) was stirred for five minutes under nitrogen at room temperature. Cyanoborohydride (0.270 g, 4.29 mmol) was added, and the mixture was stirred at room temperature under nitrogen for two hours. Water was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel chromatography (5:5 ethyl acetate:hexanes to 4:1 dichloromethane/methanol). The desired fractions were combined and the solvent was removed under reduced pressure. Water and toluene were added and removed under reduced pressure to give pure 4-(1-hydroxy-1,3-dihydrobenzo[c][1,2]oxaborol-5-yloxy)-3-(morpholinomethyl)benzonitrile (0.399 g, 80%).

Workup

  1. stirringthe mixture was stirred at room temperature under nitrogen for two hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by silica gel chromatography (5:5 ethyl acetate:hexanes to 4:1 dichloromethane/methanol)
  7. customthe solvent was removed under reduced pressure
  8. additionWater and toluene were added
  9. customremoved under reduced pressure

Sources & evidence

ORD record
ord-d26c2743ed7f427b82a73a9d2d94c9d2
Source dataset
uspto-grants-2011_10
Patent number
US08039450B2

Reaction notes

Loading…