Methyl 1-(but-3-en-1-yl)cyclopentane-1-carboxylate → HCID 86677562, compound

HRID 2401091Notes

Reaction equation

HRID 2401091 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH:12]=C)[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].I([O-])(=O)(=O)=[O:15].[Na+]>C(O)(C)C.O.[Os](=O)(=O)(=O)=O>[CH3:1][O:2][C:3]([C:5]1([CH2:10][CH2:11][CH:12]=[O:15])[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4]

Participants

6

Reactant 2

HCID 23384162Methyl 1-(but-3-en-1-yl)cyclopentane-1-carboxylateHCID 23667635Sodium periodate

Product 1

HCID 86677562HCID 86677562, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent2×

Procedure

To a solution of 1-but-3-enyl-cyclopentanecarboxylic acid methyl ester (4.0 g, 21.5 mmol) in isopropanol (35 mL) was added a solution of sodium periodate (10.1 g, 47.3 mmol) in H2O (35 mL) followed by the addition of osmium tetroxide (16 mg, 0.065 mmol). More isopropanol (30 mL) and H2O (35 mL) were added and the resulting suspension was stirred for 24 hours and then poured onto ice/H2O (200 mL) and extracted with EtOAc (2×200 mL). The organic layers were combined and dried over Na2SO4, filtered and concentrated to provide a crude oil which was purified by flash column chromatography (10 to 60% EtOAc/heptane) to provide 2.27 g (57 yield over two steps) of the title compound as an oil.

Workup

  1. additionpoured onto ice/H2O (200 mL)
  2. extractionextracted with EtOAc (2×200 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto provide a crude oil which
  7. customwas purified by flash column chromatography (10 to 60% EtOAc/heptane)
  8. customto provide

Sources & evidence

ORD record
ord-e93137b2f41d4905bbc0272e54ff0219
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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