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Boron trifluoride → 1-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

HRID 1363381
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1363381
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[BH4-].[Na+].B(F)(F)F.C1C[O:36]CC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][CH:12]([C:15]3[C:20]([O:21][CH3:22])=[CH:19][C:18]([O:23][CH3:24])=[CH:17][C:16]=3[O:25][CH3:26])[CH:13]([OH:36])[CH2:14]2)=[CH:7][CH:8]=1
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Komponenten

5

Edukt 4

HCID 6356Boron trifluorideHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 669341641,2,3,6-Tetrahydro-1-(4-methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)pyridine

Produkt 1

HCID 669340611-(4-Methoxyphenyl)-4-(2,4,6-trimethoxyphenyl)piperidin-3-ol

Reaktionsbedingungen

Temperatur
52.5 °C

Versuchsvorschrift

Compound of example 118 (15 g, 42 mmol) was subjected to hydroboration using NaBH4 (2.7 g, 71.4 mmol) and BF3-etherate (12.6 g, 88.8 mmol) in THF (50 mL). Excess diborane was destroyed by the addition of water. Conc. HCl (15 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. It was cooled to room temperature The resulting mixture was made basic (pH 12-14) using an aqueous 50% NaOH solution. 30% H2O2 (9 mL) was added and the reaction mixture was stirred at 50-55° C. for 1 h. The reaction mixture was processed as described in example 2 to obtain the title compound.

Aufarbeitung

  1. customExcess diborane was destroyed by the addition of water
  2. additionConc. HCl (15 mL) was added
  3. temperatureIt was cooled to room temperature The resulting mixture
  4. addition30% H2O2 (9 mL) was added
  5. stirringthe reaction mixture was stirred at 50-55° C. for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-fafe500061e3499aa8c1a6f20f626e11
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07884127B2

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