Trifluoroacetic acid → 1-(4-(Azetidin-3-yloxy)benzyl)pyrrolidine

HRID 1035165노트

반응식

HRID 1035165 반응식
[N:1]1([CH2:6][C:7]2[CH:24]=[CH:23][C:10]([O:11][CH:12]3[CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13]3)=[CH:9][CH:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:14]1[CH2:13][CH:12]([O:11][C:10]2[CH:23]=[CH:24][C:7]([CH2:6][N:1]3[CH2:2][CH2:3][CH2:4][CH2:5]3)=[CH:8][CH:9]=2)[CH2:15]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 58043117Tert-butyl 3-(4-(pyrrolidin-1-ylmethyl)phenoxy)azetidine-1-carboxylate

생성물 1

HCID 670165201-(4-(Azetidin-3-yloxy)benzyl)pyrrolidine수율 86.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1A (5.2 g, 15.5 mmol) in DCM (50 mL) was treated with TFA (10 g, 88 mmol) and stirred at RT for 17 h. The reaction mixture was concentrated and then co-evaporated using DCM. The residue was dissolved in water and the pH adjusted to pH 10 by adding NaOH. The solution was extracted several times with DCM and the organic solutions were filtered through a phase separator. The solvent was removed by evaporation. There was obtained 3.1 g (85%) of 1B as an oil. 1H NMR (500 MHz, CDCl3): δ 1.69-1.83 (m, 4H), 2.43-2.57 (m, 4H), 3.53 (s, 2H), 3.73-3.81 (m, 2H), 3.87-3.92 (m, 2H), 4.93-5.01 (m, 1H), 6.68 (d, 2H), 7.20 (d, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionThe residue was dissolved in water
  3. additionby adding NaOH
  4. extractionThe solution was extracted several times with DCM
  5. filtrationthe organic solutions were filtered through a phase separator
  6. customThe solvent was removed by evaporation

출처 및 근거

ORD 기록
ord-4420dbdacbd1460d837bd5aa37816600
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546375B2

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