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

HRID 1367504

Reaction equation

HRID 1367504 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 92152Silver(II) oxideCatalyst

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-bd4a922d77d947ea9da40398bae20711
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Linked notes

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