Triacetoxyperiodinane → hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[methyl-(9-oxo-nonyl)amino]bicyclo[2.2.1]hept-2-yl ester

HRID 1670899Notes

Reaction equation

HRID 1670899 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]([CH3:56])[C@H:34]1[C@H:38]2[CH2:39][CH2:40][C@@H:35]1[C@H:36]([O:41][C:42](=[O:55])[C:43]([OH:54])([C:49]1[S:50][CH:51]=[CH:52][CH:53]=1)[C:44]1[S:45][CH:46]=[CH:47][CH:48]=1)[CH2:37]2.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:56][N:33]([CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH:24]=[O:23])[C@H:34]1[C@H:38]2[CH2:39][CH2:40][C@@H:35]1[C@H:36]([O:41][C:42](=[O:55])[C:43]([OH:54])([C:49]1[S:50][CH:51]=[CH:52][CH:53]=1)[C:44]1[S:45][CH:46]=[CH:47][CH:48]=1)[CH2:37]2

Participants

5

Reactant 3

HCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 67349318Hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[(9-hydroxy-nonyl)-methyl-amino]-bicyclo[2.2.1]hept-2-yl ester

Product 1

HCID 86642393hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[methyl-(9-oxo-nonyl)amino]bicyclo[2.2.1]hept-2-yl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (450 mg, 1.06 mmol) was added to a solution of hydroxy-di-thiophen-2-yl-acetic acid (1S,2R,4S,7S)-7-[(9-hydroxy-nonyl)-methyl-amino]-bicyclo[2.2.1]hept-2-yl ester (370 mg, 0.732 mmol) in dry DCM (3 mL) at 0° C., and the reaction mixture allowed to warm to RT. After 1 h at RT the reaction mixture was treated with satd NaHCO3 (aq) and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), filtered, and concentrated to dryness. The residue was triturated with ether, and the solids removed by filtration. The filtrate was concentrated to afford an orange/brown viscous oil and used directly without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was triturated with ether
  7. customthe solids removed by filtration
  8. concentrationThe filtrate was concentrated
  9. customto afford an orange/brown viscous oil
  10. customused directly without further purification

Sources & evidence

ORD record
ord-72b108a69b9e42c1b260d34a5fea4ab6
Source dataset
uspto-grants-2011_08
Patent number
US07994211B2

Reaction notes

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