1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate

HRID 338938Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338938
[OH:1][C@@H:2]1[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.Cl[C:16]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[O:1][C@@H:2]2[C@@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]2)=[CH:30][CH:29]=1

Komponenten

4

Edukt 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 13329885tert-butyl (3S,4S)-3,4-dihydroxypyrrolidine-1-carboxylate

Produkt 1

HCID 86707461(3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylateAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of (3S,4S)-tert-butyl 3,4-dihydroxypyrrolidine-1-carboxylate (2.79 g, 13.7 mmol) in anhydrous pyridine (144 mL) was added 4,4′-(chloro(phenyl)methylene)bis(methoxybenzene) (5.43 g 15.2 mmol) and the resulting mixture stirred at ambient temperature for 4 days. The reaction was quenched with methanol (10 mL) and concentrated under reduced pressure. The residue was stirred in diethyl ether (150 mL) and the solid which precipitated was collected by filtration. The filtrate was concentrated under reduced pressure and purified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane) to afford (3S,4S)-tert-butyl 3-(bis(4-methoxyphenyl)(phenyl)methoxy)-4-hydroxypyrrolidine-1-carboxylate (4.48 g, 65%).

Aufarbeitung

  1. customThe reaction was quenched with methanol (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. stirringThe residue was stirred in diethyl ether (150 mL)
  4. customthe solid which precipitated
  5. filtrationwas collected by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. custompurified by column chromatography (Biotage, 40M; 1% methanol:dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-37b5001076fa4bceb9a55543c9b63e49
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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