Trifluoroacetic acid → 1-(Cyanomethyl)indoline

HRID 2057359노트

반응식

HRID 2057359 반응식
[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)#[N:2].FC(F)(F)C(O)=O.N1C2C(=CC=CC=2)C=C1.B>B.C1COCC1>[C:1]([CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)#[N:2]

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 122309041H-Indole-1-acetonitrileHCID 178419140HCID 178419140, 화합물

생성물 1

HCID 124246651-(Cyanomethyl)indoline

시약·촉매·용매 1

HCID 2723981Borane;tetrahydrofuran용매

실험 절차

In an operation carried out in a manner similar to that described in Example XIV, 105 milligrams of 1-cyanomethyl indole was dissolved in 1.5 milliliters of 1 M BH3.THF under nitrogen. Then, while cooling and stirring in an ice bath, 1.0 milliliter of trifluoroacetic acid was added dropwise to the indole-borane reagent mixture and after completion of the addition, stirring was continued for 1.5 hours while maintaining nitrogen atmosphere to obtain a 1-cyanomethyl-2,3-dihydroindole product in the reaction mixture. The product was recovered by adding first water, then methylene chloride, stirring the mixture (about 15 minutes), making alkaline (pH>9), separating the methylene chloride solution, drying the latter and evaporating the solvent from the dried solution in vacuo.

후처리

  1. temperatureThen, while cooling
  2. additionafter completion of the addition
  3. stirringstirring
  4. temperaturewhile maintaining nitrogen atmosphere

출처 및 근거

ORD 기록
ord-855f82f2e688447391a16ae73904aff6
출처 데이터셋
uspto-grants-1980_07
특허 번호
US04210590

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