Sodium periodate → HCID 58557804, compound

HRID 1969568Notes

Reaction equation

HRID 1969568 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][C@H:5]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:4]1)[CH3:2].I([O-])(=O)(=O)=[O:17].[Na+]>CC#N.O.CCOC(C)=O.O.[Ru](Cl)(Cl)Cl>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][C@H:5]1[CH2:6][C@H:7]([C:8]([OH:17])=[O:9])[C@H:3]([CH2:1][CH3:2])[CH2:4]1)[CH3:15]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 58557162HCID 58557162, compound

Product 1

HCID 58557804HCID 58557804, compoundYield 101%

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of ethyl 2-((1R,3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentyl)acetate (0.140 g, 0.653 mmol) in MeCN (2 mL), water (4 mL) and EtOAc (2 mL) was added sodium periodate (0.349 g, 1.633 mmol) followed by ruthenium(III) chloride hydrate (0.0015 g, 0.0065 mmol). After about 2 h, the reaction mixture was diluted with EtOAc (20 mL) and water (10 mL). The organic layer was separated and extracted with aqueous NaOH (1 N, 10 mL). The pH of the aqueous layer was adjusted to about 1 with concd HCl and extracted with EtOAc (20 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concd in vacuo to provide (1S,2R,4R)-4-(2-ethoxy-2-oxoethyl)-2-ethylcyclopentanecarboxylic acid (0.150 g, 101%) as an oil which was used without further purification. 1H NMR (600 MHz, CDCl3) δ 10.68 (bs, 1H), 4.13 (q, J=7.1 hz, 2H), 2.99-2.95 (m, 1H), 2.76-2.64 (m, 1H), 2.31 (d, J=7.6 Hz, 2H), 2.24 (ddd, J=13.5, 8.7, 4.8 Hz, 1H), 2.18-2.11 (m, 1H), 1.81 (dt, J=13.0, 8.4 Hz, 1H), 1.55-1.45 (m, 3H), 1.31-1.27 (m, 1H), 1.25 (t, J=7.0 Hz, 3H), (t, J=7.4 Hz, 3H).

Workup

  1. customThe organic layer was separated
  2. extractionextracted with aqueous NaOH (1 N, 10 mL)
  3. extractionextracted with EtOAc (20 mL)
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. filtrationfiltered

Sources & evidence

ORD record
ord-99daf20d7864450fab6f3c2f159ff2c8
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

Loading…