Potassium Chloride → (1S,2S)-1-hydroxy-2-carboethoxy-5-methoxyindane

HRID 1586302Notes

Reaction equation

HRID 1586302 reaction equation
O=C[C@@H]([C@H]([C@@H]([C@@H](CO)O)O)O)O.OP([O-])(O)=O.[K+].OP([O-])([O-])=O.[K+].[K+].[Cl-].[K+].[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:36](=[CH:37][CH:38]=1)[C:35](=[O:39])[CH:34]([C:40]([O:42][CH2:43][CH3:44])=[O:41])[CH2:33]2.COC1C=CC(C=O)=CC=1>C(O)C>[OH:39][C@@H:35]1[C:36]2[C:32](=[CH:31][C:30]([O:29][CH3:28])=[CH:38][CH:37]=2)[CH2:33][C@@H:34]1[C:40]([O:42][CH2:43][CH3:44])=[O:41]

Participants

8

Reactant 6

HCID 4873Potassium ChlorideHCID 24450Potassium Phosphate, DibasicHCID 312444-MethoxybenzaldehydeHCID 107526(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanalHCID 516951Monobasic potassium phosphateHCID 12177975ethyl 5-methoxy-1-oxo-2,3-dihydro-1H-indene-2-carboxylate

Product 1

HCID 57081514(1S,2S)-1-hydroxy-2-carboethoxy-5-methoxyindaneYield 84.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Colletotrichum gloeosporioides is cultured according to the method of Buisson and Azerad (Tet. Lett. 27, 2631-2634 (1986), herein incorporated by reference) in one liter of a medium of glucose (30 grams), KH2PO4 (1 gram), K2HPO4 (2 grams), corn steep liquor (10 grams) MgSO4.7H2O (0.5 gram), NaNO3 (2 grams), FeSO4.7H2O (0.02 gram), and KCl (0.5 gram) with rotary shaking at 25° C. Two grams of 5-methoxy-2-carboethoxy-1-indanone is dissolved in 2 ml of 95% ethanol, the resulting solution is added to the culture, and shaking is resumed. The reaction is followed by TLC (staining with anisaldehyde) to monitor the consumption of starting material and the production of product alcohol. After approximately 48 hours the reaction is judged complete, and the reaction is terminated by removing from the shaker and adding 20-30 grams of Celite. The resulting suspension is suction filtered through a pad of Celite and the clear yellow filtrate is extracted with ethyl acetate (4×200 ml). The extracts are combined, dried over MgSO4, filtered, and rotary evaporated to leave 1.7 grams of (1S,2S)-1-hydroxy-2-carboethoxy-5-methoxyindane as a yellow oil. The chiral purity of the product is greater than 98% as judged by chiral chromatography.

Workup

  1. additionthe resulting solution is added to the culture
  2. customthe consumption of starting material
  3. customthe reaction is terminated
  4. customby removing from the shaker
  5. additionadding 20-30 grams of Celite
  6. filtrationfiltered through a pad of Celite
  7. extractionthe clear yellow filtrate is extracted with ethyl acetate (4×200 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customrotary evaporated

Sources & evidence

ORD record
ord-6ce6d43c32424e5594894cf3d469a28d
Source dataset
uspto-grants-1999_08
Patent number
US05942644

Reaction notes

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