Methanol → HCID 86602718, Verbindung

HRID 1178859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1178859
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10]1.[CH3:31][OH:32].[BH4-].[Na+].[OH2:35].[CH3:36][NH2:37]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[F:1][C:2]([F:30])([F:29])[C:31]([OH:35])=[O:32].[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:24]=1)[CH2:6][O:7][CH2:8][C:9]1([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][CH2:12][CH:11]([NH:37][CH3:36])[CH2:10]1

Komponenten

7

Edukt 5

HCID 887MethanolHCID 962WaterHCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 219731213-((3,5-Bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone

Produkt 1

HCID 86602718HCID 86602718, VerbindungAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11026Titanium isopropoxideKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 3-((3,5-bis(trifluoromethyl)benzyloxy)methyl)-3-phenylcyclohexanone (10 mg) in methylamine (2.0 M solution in THF, 0.11 mL) at room temperature was added titanium(IV) isopropoxide (0.02 mL) and the resulting solution was heated at 80° C. in a sealed vial for 1.5 h. The solution was cooled to room temperature, 0.1 mL methanol was added followed by sodium borohydride (4.4 mg), and the resulting suspension was stirred at room temperature for 2 h. H2O was added to quench the reaction and the mixture was extracted with dichloromethane 3 times. The combined organic layers were concentrated and residue was purified by preparative HPLC to give the title compound (8 mg, 62% yield). 1H NMR (500 MHz, CD3OD) δ 1.39 (1H, m), 1.56 (1H, m), 1.72 (1H, m), 1.88 (1H, m), 2.14 (1H, m), 2.39 (1H, m), 2.61 (1H, m), 2.70 (3H, d, J=25 Hz), 2.71 (1H, m), 3.44 (1H, d, J=5 Hz), 3.79 (2H, dd, J=10, 60 Hz), 4.49-4.60 (2H, m), 7.21-7.28 (1H, m), 7.33 (1H, t, J=8 Hz), 7.38-7.46 (3H, m), 7.65 (1H, s), 7.72 (1H, s), 7.82 (1H, d, J=10 Hz). HPLC purity (retention time): 95% (2.05 min, method C). MS: 446.49 (MH+).

Aufarbeitung

  1. temperatureThe solution was cooled to room temperature
  2. customto quench
  3. customthe reaction
  4. extractionthe mixture was extracted with dichloromethane 3 times
  5. concentrationThe combined organic layers were concentrated
  6. customresidue was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-d32c2ab6716b4a8c990588e91b49b3fe
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07276631B2

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