Hydrochloric Acid → HCID 18401805, compound

HRID 377285Notes

Reaction equation

HRID 377285 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([CH3:11])[N:6]([C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:5]2.C([Li])CCC.C([O:39][B:40](OC(C)C)[O:41]C(C)C)(C)C.Cl>O1CCCC1.CCCCCC>[CH3:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([B:40]([OH:41])[OH:39])=[CH:10][CH:9]=2)[CH2:5][N:6]1[C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 21531Triisopropyl borateHCID 18629350HCID 18629350, compoundHCID 178418339Butyllithium

Product 1

HCID 18401805HCID 18401805, compoundYield 80.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-72 °C

Procedure

In 75 ml of anhydrous tetrahydrofuran was dissolved 15.0 g of (+)-5-bromo-1-methyl-2-trityliso-indoline, and the solution was cooled to -72° C. under a nitrogen atmosphere, after which 22.3 ml of a 1.63 M solution of n-butyllithium in n-hexane was added dropwise thereto over a period of 15 minutes, and the resulting mixture was stirred at the same temperature for 1 hour. To the reaction mixture was added dropwise 7.45 g of triisopropoxyborane at -72° C. over a period of 20 minutes, and the resulting mixtuere was stirred at the same temperature for 30 minutes. The reaction mixture was added to 75 ml of ice water and the pH was adjusted to 6.8 with lN hydrochloric acid, after which the organic layer was separated. The organic layer obtained was washed with water, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. Cyclohexane was added to the resulting residue and the crystals were collected by filtration to obtain 11.2 g ofcolorless (+)-1-methyl-2-tritylisoindoline-5-boronic acid.

Workup

  1. stirringthe resulting mixtuere was stirred at the same temperature for 30 minutes
  2. customafter which the organic layer was separated
  3. customThe organic layer obtained
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationdistilled under reduced pressure
  7. customto remove the solvent
  8. additionCyclohexane was added to the resulting residue
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-a66decf5b1d54b8381f43082dad26a21
Source dataset
uspto-grants-2000_02
Patent number
US06025370

Reaction notes

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