Phenylboronic Acid → HCID 66751247, compound

HRID 2043326Notes

Reaction equation

HRID 2043326 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:10][CH2:11][CH:12]1[O:16][CH2:15][CH2:14][O:13]1>ClCCl>[O:13]1[CH2:14][CH2:15][O:16][CH:12]1[CH2:11][NH:10][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 66827Phenylboronic AcidHCID 108553941-(1,3-Dioxolan-2-yl)methanamine

Product 1

HCID 66751247HCID 66751247, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of phenylboronic acid (0.5 g, 4.1 mmol), copper(II)-acetate-1-hydrate (0.041 g, 0.21 mmol) and molecular sieves (1.5 g, size 0.4 nm, powdered) in dichloromethane (12 ml) was stirred for 5 min. Then 2-(aminomethyl)-1,3-dioxolane (0.211 g, 2.05 mmol) was added and oxygen was bubbled through the mixture for 5 min. The vessel was closed and shaken overnight at room temperature. For workup ethyl acetate (50 ml) and 1 M sodium bicarbonate solution (30 ml) were added and the mixture was shaken. The organic layer was separated, dried over magnesium sulfate and evaporated. The residue was purified using flash chromatography (SiO2; eluent: heptane/ethyl acetate=90:10) to yield a light yellow oil (105 mg, 14%); MS (EI): 179.1 (M+.).

Workup

  1. customoxygen was bubbled through the mixture for 5 min
  2. customThe vessel was closed
  3. stirringshaken overnight at room temperature
  4. additionFor workup ethyl acetate (50 ml) and 1 M sodium bicarbonate solution (30 ml) were added
  5. stirringthe mixture was shaken
  6. customThe organic layer was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated
  9. customThe residue was purified

Sources & evidence

ORD record
ord-4dc396cfeb5a4c89bbcbe24d130b4b7c
Source dataset
uspto-grants-2013_11
Patent number
US08586617B2

Reaction notes

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