2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 58438635, compound

HRID 1898580Notes

Reaction equation

HRID 1898580 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:8]2[CH2:13][CH:12]3[CH:10]([CH2:11]3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.C(O[B:23]1[O:27][C:26]([CH3:29])([CH3:28])[C:25]([CH3:31])([CH3:30])[O:24]1)(C)C>C1COCC1>[CH3:30][C:25]1([CH3:31])[C:26]([CH3:29])([CH3:28])[O:27][B:23]([C:2]2[CH:3]=[C:4]([N:8]3[CH2:13][CH:12]4[CH:10]([CH2:11]4)[CH2:9]3)[CH:5]=[CH:6][CH:7]=2)[O:24]1

Participants

5

Reactant 3

HCID 50177412-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 57516630HCID 57516630, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58438635HCID 58438635, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

3-(3-Bromo-phenyl)-3-aza-bicyclo[3.1.0]hexane (2.0 g, 8.4 mmol) was dissolved in 40 mL of THF and cooled to −78° C. in a dry ice acetone bath. tert-Butyl lithium (1.7 M solution in pentane, 14.8 mL, 25.2 mmol) was added dropwise and the reaction was stirred at −78° C. for 15 min. 2-Isopropoxy-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.4 mL, 16.8 mmol) was added and the reaction was stirred at −78° C. for 2 h. The reaction was quenched with saturated aqueous ammonium chloride and warmed to room temperature. Water was added and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried, filtered and concentrated. The crude residue was chromatographed using a gradient of 0% to 10% ethyl acetate/heptane to give 1.93 g (81%) of 3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3-aza-bicyclo[3.1.0]hexane as a white solid.

Workup

  1. stirringthe reaction was stirred at −78° C. for 2 h
  2. customThe reaction was quenched with saturated aqueous ammonium chloride
  3. temperaturewarmed to room temperature
  4. additionWater was added
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted twice with ethyl acetate
  7. customThe combined organic layers were dried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude residue was chromatographed

Sources & evidence

ORD record
ord-9849237030ff48ecb7c9d94bf318f83b
Source dataset
uspto-grants-2013_08
Patent number
US08518945B2

Reaction notes

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