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

HRID 1798553ノート

反応式

HRID 1798553 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-73da5202ab4c4a2f9f368d9674fbcfa3
出典データセット
uspto-grants-2013_01
特許番号
US08343966B2

反応ノート

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