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

HRID 1246922노트

반응식

HRID 1246922 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

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 Na2SO4, 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.

후처리

  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 Na2SO4
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-694988cde2784ad6a4c495715c0efa2f
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129228B2

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