Piperidine → 3-Methoxy-4-piperidin-1-ylmethylphenol

HRID 1505882Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1505882
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([O:10][CH3:11])[CH:3]=1.[NH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:11][O:10][C:4]1[CH:3]=[C:2]([OH:1])[CH:9]=[CH:8][C:5]=1[CH2:6][N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 5195414-Hydroxy-2-MethoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 582667373-Methoxy-4-piperidin-1-ylmethylphenolAusbeute 30,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11026Titanium isopropoxideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a pre-stirred solution of 4-hydroxy-2-methoxybenzaldehyde (1.02 g, 6.7 mmol), titanium isopropoxide (2.14 mL, 7.0 mmol) and piperidine (0.70 mL, 7.0 mmol) in DCM (20 mL) was added sodium triacetoxyborohydride (2.84 g, 13.4 mmol) in portions. After 3 h the reaction mixture was quenched by the addition of methanol (1.0 mL) and then the solvents were removed under reduced pressure to afford a residue. The resultant residue was then loaded onto an SCX-2 cartridge (10 g) and eluted with 2N ammonia in methanol to afford the title compound (456 mg, 30%). 1H NMR (CD3OD, 300 MHz): 7.17 (d, J=8.3 Hz, 1H), 6.51 (d, J=2.3 Hz, 1H), 6.43 (dd, J=8.2, 2.2 Hz, 1H), 4.07 (s, 2H), 3.84 (s, 3H), 3.16-2.99 (m, 4H), 1.84-1.73 (m, 4H), 1.67-1.56 (m, 2H).

Aufarbeitung

  1. customAfter 3 h the reaction mixture was quenched by the addition of methanol (1.0 mL)
  2. customthe solvents were removed under reduced pressure
  3. customto afford a residue
  4. washeluted with 2N ammonia in methanol

Quellen und Nachweise

ORD-Eintrag
ord-027c4cee7b1c42b4847c50d71cc53345
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216980B2

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