Hexane → 3-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

HRID 1594853Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1594853
[Li]CCCC.CCCCCC.CC1(C)CCCC(C)(C)N1.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([CH:30]2[CH2:36][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[C:31]2=[O:38])[CH:27]=[CH:28][CH:29]=1.[CH3:39][O:40][CH2:41]I>C1COCC1>[CH3:39][O:40][CH2:41][C:30]1([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=2)[CH2:36][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[C:31]1=[O:38]

Komponenten

7

Edukt 5

HCID 8058HexaneHCID 130352,2,6,6-TetramethylpiperidineHCID 139376Iodomethyl methyl etherHCID 2727906hexahydro-3-(3-methoxyphenyl)-1-methyl-2H-azepin-2-oneHCID 178418339Butyllithium

Produkt 1

HCID 217062403-Methoxymethyl-3-(3-methoxy-phenyl)-1-methyl-azepan-2-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To 1.6 M n-BuLi in hexane (3.38 mL, 5.42 mmol) at 0° C. was added a solution of 2,2,6,6-tetramethyl piperidine (0.91 mL, 5.42 mmol) in anh. THF (10 mL) over 5 min. A solution of 3-(3-methoxy-phenyl)-1-methyl-azepan-2-one (as described in Example 4, Step A) (0.632 g, 2.71 mmol) in anhydrous THF (10 mL) was added and stirred OC for 1 h. Iodomethyl methyl ether (0.275 mL, 3.25 mmol) was added. After stirring for 30 min, the reaction was quenched with H2O, concentrated in vacuo, diluted with EtOAc, washed with 5N HCl (100 mL), water and brine. The organic layer was dried (MgSO4) and concentrated to give the title compound.

Aufarbeitung

  1. stirringAfter stirring for 30 min
  2. customthe reaction was quenched with H2O
  3. concentrationconcentrated in vacuo
  4. additiondiluted with EtOAc
  5. washwashed with 5N HCl (100 mL), water and brine
  6. dry with materialThe organic layer was dried (MgSO4)
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-ec2b0b360ba74e30beba54301bd0e5f9
Quelldatensatz
uspto-grants-2001_09
Patentnummer
US06284755B1

Notizen zur Reaktion

Wird geladen…