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

HRID 1425710노트

반응식

HRID 1425710 반응식
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

참가 물질

4

반응물 2

HCID 11776Triphenylphosphine2회HCID 858170813-[4-(Azidomethyl)phenyl]-3-(Trifluoromethyl)-3H-Diazirine

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-623448c257da45cab6e813125eb7706f
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933065B2

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