Methyl iodide → (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethyl-cyclopentanecarboxylic acid ethyl ester

HRID 1367504

Reaktionsgleichung

Reaktionsgleichung von HRID 1367504
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH2:8][C@H:7]1[CH2:19][OH:20])=[O:5])[CH3:2].I[CH3:22]>[Ag]=O>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([O:11][Si:12]([C:15]([CH3:16])([CH3:18])[CH3:17])([CH3:13])[CH3:14])[CH2:8][C@H:7]1[CH2:19][O:20][CH3:22])=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 6328Methyl iodideHCID 59619451(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester

Produkt 1

HCID 66918779(1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methoxymethyl-cyclopentanecarboxylic acid ethyl esterAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 92152Silver(II) oxideKatalysator

Versuchsvorschrift

To a solution of (1R,2R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-cyclopentanecarboxylic acid ethyl ester (Example 68/69 step 4, epimeric mixture, 509 mg) in iodomethane (24 g) was added silver oxide (3.9 g) in several portions over 8 days. After 12 days at room temperature, the reaction mixture was concentrated in vacuo, diluted with dichloromethane, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/EtOAc (1:0 to 9:1 v/v) as eluant to afford the title compound (228 mg, 43%) as light yellow oil. MS (EI): 317.1 (M+H)+.

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with dichloromethane
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel with a gradient of cyclohexane/EtOAc (1:0 to 9:1 v/v) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-bd4a922d77d947ea9da40398bae20711
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893099B2

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