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

HRID 1035165ノート

反応式

HRID 1035165 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4420dbdacbd1460d837bd5aa37816600
出典データセット
uspto-grants-2013_10
特許番号
US08546375B2

反応ノート

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