3-Fluorophenol → Tert-butyl 4-(3-fluorophenoxy)piperidine-1-carboxylate

HRID 43346

Reaktionsgleichung

Reaktionsgleichung von HRID 43346
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[F:15][C:16]1[CH:17]=[C:18](O)[CH:19]=[CH:20][CH:21]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:15][C:16]1[CH:21]=[C:20]([O:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 3

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Produkt 1

HCID 57699520Tert-butyl 4-(3-fluorophenoxy)piperidine-1-carboxylateAusbeute 94,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 1,1-dimethylethyl 4-hydroxy-1-piperidinecarboxylate (24 g, 112 mmol), 3-fluorophenol (5.6 g, 59 mmol) and triphenylphosphine (31.4 g, 118 mmol) in THF (100 ml) was added di-isopropylazodicarboxylate (23.3 ml, 118 mmol). The reaction was stirred at room temperature for 3 days and then the solvent removed in vacuo. The residue was diluted with DCM, hexane was added and the resultant white precipitate filtered off. The filtrate was concentrated in vacuo and purified by chromatography. Elution with DCM gave the title compound (16.4 g, 87% pure). δH (CDCl3, 250 MHz) 1.47 (9H, s), 1.76 (2H, m), 1.92 (2H, m), 3.35 (2H, ddd), 3.69 (2H, ddd), 4.44 (1H, m), 6.65 (3H, m), 7.20 (1H, m).

Aufarbeitung

  1. customthe solvent removed in vacuo
  2. additionThe residue was diluted with DCM, hexane
  3. additionwas added
  4. filtrationthe resultant white precipitate filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by chromatography
  7. washElution with DCM

Quellen und Nachweise

ORD-Eintrag
ord-93e31a61c21a41989b70d85c7f8821d7
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536182B2

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