Acetic Acid → 3-Aminomethyl-5-methyl-phenyl boronic acid

HRID 1798553Notes

Reaction equation

HRID 1798553 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([B:10]([OH:12])[OH:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1)=O.[NH3:13].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[NH2:13][CH2:1][C:3]1[CH:4]=[C:5]([B:10]([OH:12])[OH:11])[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 5049666Sodium triacetoxyborohydrideHCID 16217687(3-Formyl-5-methylphenyl)boronic acid

Product 1

HCID 866336493-Aminomethyl-5-methyl-phenyl boronic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-Formyl-5-methylphenylboronic acid (1 eq, 3.05 mmol, 0.5 g) in dry DCM (5 ml) under an inert atmosphere of argon is treated with ammonia solution 35% (1.1 eq, 3.35 mmol, 0.185 ml) followed by acetic acid (1.1 eq, 3.35 mmol, 0.192 ml) and NaBH(OAc)3 (1.2 eq, 3.66 mmol, 0.776 mg) and the resulting mixture is stirred at room temperature overnight. The reaction is quenched by addition of acetonitrile and filtered under vacuum. The filtrate is concentrated in vacuo to afford the title compound which is used without further purification.

Workup

  1. customThe reaction is quenched by addition of acetonitrile
  2. filtrationfiltered under vacuum
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-73da5202ab4c4a2f9f368d9674fbcfa3
Source dataset
uspto-grants-2013_01
Patent number
US08343966B2

Reaction notes

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