p-(Trifluoromethoxy)phenyl isocyanate → HCID 49780163, Verbindung

HRID 929504Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 929504
[F:1][C:2]([F:14])([F:13])[O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1.[C:15]([N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C1COCC1>[F:1][C:2]([F:13])([F:14])[O:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:12])[NH:28][CH:25]2[CH2:24][CH2:23][N:22]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:27][CH2:26]2)=[CH:8][CH:9]=1

Komponenten

4

Edukt 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 12682914-Amino-1-Boc-piperidine

Produkt 1

HCID 49780163HCID 49780163, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

4-Trifluoromethoxyphenyl isocyanate (1.03 g, 5 mmol) was dissolved in dry THF (10 mL) and cooled in an ice bath. A solution of N—BOC-4-aminopiperidine (781 mg, 5 mmol) in dry THF (10 mL) was slowly added. The reaction was allowed to warm to RT and stir for 12 hours. The solvent was removed and the residue chromatographed from ethyl acetate to give intermediate 41 (1.71 g, 95%) as a white solid: Mp 160-162° C. 1H NMR (500 MHz, DMSO-d6) δ 8.54 (s, 1H), 7.47 (d, J=9.0 Hz, 2H), 7.21 (d, J=8.6 Hz, 2H), 6.22 (d, J=7.6 Hz, 1H), 3.81 (d, J=13.0 Hz, 2H), 3.67-3.59 (m, 1H), 2.90 (s, 2H), 1.79 (dd, J=12.6, 2.5 Hz, 2H), 1.40 (s, 9H), 1.25 (dq, J=12.1, 3.9 Hz, 2H). HRMS calculated for C18H24F3N3O4−H+402.1641. found (ESI(−), [M−H]) 402.1612.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. customThe solvent was removed
  3. customthe residue chromatographed from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-62d4a2c0b0604116bcccef6b7b572e44
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09296693B2

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