Hydrochloric Acid → 4-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride

HRID 535778ノート

反応式

HRID 535778 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:23])[CH:10]([NH:15]C(=O)OC(C)(C)C)[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][CH:4]=1)#[N:2].[ClH:24]>CO>[ClH:24].[NH2:15][CH:10]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:9]([C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1)=[O:23]

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 68404944tert-Butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate

生成物 1

HCID 682779744-(2-Amino-3,3-dimethylbutanoyl)benzonitrile hydrochloride収率 93%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

tert-Butyl 1-(4-chlorophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (Example 2a, 2.30 g, 7.06 mmol) and Zn(CN)2 (0.87 g, 7.4 mmol) were dissolved in DMF (20 mL) under N2 (g). Pd(PPh3)4 (0.86 g, 0.74 mmol) was added and the mixture was heated at 130° C. overnight. The mixture was cooled to rt, diluted with water and extracted with EtOAc. The organic phase was washed with brine, dried over Na2SO4 and evaporated. The product was purified on a silica column (EtOAc:hexane 1:10) to give tert-butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (961 mg, 43%). tert-Butyl 1-(4-cyanophenyl)-3,3-dimethyl-1-oxobutan-2-ylcarbamate (961 mg, 3.04 mmol) was dissolved in 1.25 M HCl in MeOH at 0° C. and the mixture was stirred at rt for 8 h. The solvent was removed and the residue dried in vacuo to give 4-(2-amino-3,3-dimethyl-butanoyl)-benzonitrile hydrochloride (110 mg, 93%).

後処理

  1. customThe solvent was removed
  2. customthe residue dried in vacuo

出典と根拠

ORDレコード
ord-a26bf46d8f2f4061a417f85c87858b11
出典データセット
uspto-grants-2014_10
特許番号
US08859556B2

反応ノート

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