Trifluoroacetic acid → 3-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzonitrile

HRID 513015ノート

反応式

HRID 513015 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([C@H:10]2[CH2:14][C@H:13]([F:15])[CH2:12][N:11]2C(OC(C)(C)C)=O)[CH:6]=[C:7]([F:9])[CH:8]=1)#[N:2].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:9][C:7]1[CH:8]=[C:3]([CH:4]=[C:5]([C@H:10]2[CH2:14][C@H:13]([F:15])[CH2:12][NH:11]2)[CH:6]=1)[C:1]#[N:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 66684286(2R,4S)-tert-butyl 2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidine-1-carboxylate

生成物 1

HCID 666849673-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2R,4S)-tert-butyl 2-(3-cyano-5-fluorophenyl)-4-fluoropyrrolidine-1-carboxylate (I-14) (0.6 g, 1.95 mmol) in DCM (2 mL) at room temperature was added TFA (2 mL). The mixture was stirred at room temperature for 2 hours. All the solvents were removed under reduced pressure. The crude was diluted with EtOAc, washed with aqueous NaHCO3 and brine, dried over sodium sulfate, filtered and concentrated to yield 3-fluoro-5-((2R,4S)-4-fluoropyrrolidin-2-yl)benzonitrile (I-15). 1H NMR (400 MHz, CDCl3) δ 7.52 (s, 1 H), 7.43-7.37 (m, 1 H), 7.24-7.20 (m, 1 H), 5.28 (dt, J=3.6, 53.6 Hz, 1 H), 4.57 (dd, J=6.4, 9.6 Hz, 1 H), 3.44-3.18 (m, 2 H), 2.63-2.50 (m, 1 H), 1.72 (dddd, J=4.4, 10.0, 14.4, 39.6 Hz, 1H). MS m/z 209.1 (M+1)+.

後処理

  1. customAll the solvents were removed under reduced pressure
  2. additionThe crude was diluted with EtOAc
  3. washwashed with aqueous NaHCO3 and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-ecb8edc9bbe446c2a22351df2990d8b3
出典データセット
uspto-grants-2015_08
特許番号
US09102671B2

反応ノート

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