Aniline → 3-Phenylaminomethyl-azepane-1-carboxylic acid benzyl ester

HRID 1839220ノート

反応式

HRID 1839220 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([CH:25]=O)[CH2:19]1)=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[BH3-]C#N.[Na+]>CC(O)=O.CO>[CH2:8]([O:15][C:16]([N:18]1[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]([CH2:25][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1)=[O:17])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

参加物

6

反応物 3

HCID 6115AnilineHCID 5003444Sodium cyanoborohydrideHCID 20598085Benzyl 3-formylazepane-1-carboxylate

生成物 1

HCID 205980843-Phenylaminomethyl-azepane-1-carboxylic acid benzyl ester

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒

実験手順

Aniline (0.126 mL, 1.38 mmol) was added to a solution of 3-formyl-azepane-1-carboxylic acid benzyl ester (147) (0.300 g, 1.15 mmol) in 5% HOAc in MeOH (11.5 mL). The reaction was stirred for approx. 20 minutes, then NaBH3CN (0.2164 g, 3.44 mmol) was slowly added and the reaction was stirred at room temperature overnight. The reaction was then concentrated in vacuo and EtOAc and a few drops of 10% NaOH were added. The organic was washed with saturated NaCl (aq), dried with NaSO4, concentrated in vacuo, to give crude 3-phenylaminomethyl-azepane-1-carboxylic acid benzyl ester (148). Compound 148 was used in the next step without further purification.

後処理

  1. stirringthe reaction was stirred at room temperature overnight
  2. concentrationThe reaction was then concentrated in vacuo and EtOAc and a few drops of 10% NaOH
  3. additionwere added
  4. washThe organic was washed with saturated NaCl (aq)
  5. dry with materialdried with NaSO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7c94a0d9c4364bd180f419607b052581
出典データセット
uspto-grants-2004_01
特許番号
US06677332B1

反応ノート

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