Triphenylphosphine → 4-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamine

HRID 1425710ノート

反応式

HRID 1425710 の反応式
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2([C:33]([F:36])([F:35])[F:34])[N:32]=[N:31]2)=[CH:26][CH:25]=1)=[N+]=[N-]>C1COCC1>[F:36][C:33]([F:34])([F:35])[C:30]1([C:27]2[CH:26]=[CH:25][C:24]([CH2:23][NH2:20])=[CH:29][CH:28]=2)[N:31]=[N:32]1

参加物

4

反応物 2

HCID 11776Triphenylphosphine2 回HCID 858170813-[4-(Azidomethyl)phenyl]-3-(Trifluoromethyl)-3H-Diazirine

生成物 1

HCID 109328304-(3-(Trifluoromethyl)-3H-diazirin-3-yl)benzenemethanamine収率 80%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Triphenylphosphine polymer bound (Fluka, cat #93094) (1.6 g/mol, 6.3 mmol) was added to an aqueous (378 μL, 21.0 mmol)/THF (10 mL) solution of 3-[4-(azidomethyl)phenyl]-3-(trifluoromethyl)-3H-diazirine (506 mg, 2.1 mmol). The mixture was shaken until the starting material was no longer evident by TLC analysis (18 h). The triphenylphosphine-based support was filtered, washed with CH2Cl2, and the filtrate was concentrated in vacuum to obtain 350 mg (80%) of a yellow oil corresponding to the free amine: 1H NMR (CDCl3) δ 1.35-1.50 (br s, NH2), 3.89 (s, CH2), 7.17 (d, J=8.2 Hz, 2 C6H4), 7.35 (d, J=8.2 Hz, 2 C6H4); 13C NMR (CDCl3): δ 28.4 (q, J=39.9 Hz, C diazirine), 45.9 (CH2NH2), 122.2 (q, J=273.2 Hz, CF3), 126.7 (C6H2), 127.5 (C6H2), 145.0 (C6H2) (one peak is overlapped with an other one).

後処理

  1. customwas no longer evident by TLC analysis (18 h)
  2. filtrationwas filtered
  3. washwashed with CH2Cl2
  4. concentrationthe filtrate was concentrated in vacuum

出典と根拠

ORDレコード
ord-623448c257da45cab6e813125eb7706f
出典データセット
uspto-grants-2015_01
特許番号
US08933065B2

反応ノート

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