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

HRID 906347

Reaktionsgleichung

Reaktionsgleichung von HRID 906347
[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 over-weekend and then the solvent was removed in vacuo. The residue was diluted with DCM, hexane was added and the resultant precipitate was filtered off. The filtrate was concentrated in vacuo and purified by column 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 was removed in vacuo
  2. additionThe residue was diluted with DCM, hexane
  3. additionwas added
  4. filtrationthe resultant precipitate was filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. custompurified by column chromatography
  7. washElution with DCM

Quellen und Nachweise

ORD-Eintrag
ord-653c2f53d16b4ac2a8f39fa0090f1622
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012981B2

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