Triphenylphosphine → tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate

HRID 59884

Reaktionsgleichung

Reaktionsgleichung von HRID 59884
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].O[C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C@@H:16]1[CH2:17][CH2:12][CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1)[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 667552-EthoxyphenolHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

Produkt 1

HCID 131737068tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylateAusbeute 45,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-ethoxyphenol (13.72 g, 99 mmol), tert-butyl (S)-3-hydroxypiperidine-1-carboxylate (20 g, 99 mmol), and triphenylphosphine (29 g, 111 mmol) in toluene (150 mL) at 20-25° C. was added a solution of DIAD (20 mL, 104 mmol) in toluene (50 mL) over 2 hours. After 2 hours, the reaction mixture was filtered and washed with diethyl ether (300 mL). The filtrate was washed with 3N NaOH (150 mL), dried over Na2SO4, and concentrated. The crude residue was purified via column chromatography to afford tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate (14.6 g, 45%). MS (ES+) 222.2 (M-100+H).

Aufarbeitung

  1. filtrationthe reaction mixture was filtered
  2. washwashed with diethyl ether (300 mL)
  3. washThe filtrate was washed with 3N NaOH (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude residue was purified via column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-84c2c17968264ec79a61826a50901a96
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440949B2

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