Pyridine → (1S,4aS,7aR)-7-[2-(acetoxy)ethyl]-1-[1-(ethoxy)ethoxy]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester

HRID 1976370Notes

Reaction equation

HRID 1976370 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][CH2:21][OH:22])[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4].N1C=CC=CC=1.[C:29](OC(=O)C)(=[O:31])[CH3:30]>ClCCl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][C:3]([C:5]1[C@H:6]2[CH2:19][CH:18]=[C:17]([CH2:20][CH2:21][O:22][C:29](=[O:31])[CH3:30])[C@@H:7]2[C@H:8]([O:11][CH:12]([O:14][CH2:15][CH3:16])[CH3:13])[O:9][CH:10]=1)=[O:4]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57042520(1S,4aS,7aR)-1-[1-(ethoxy)ethoxy]-7-[2-(hydroxy)ethyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylester

Product 1

HCID 57302883(1S,4aS,7aR)-7-[2-(acetoxy)ethyl]-1-[1-(ethoxy)ethoxy]-1,4a,5,7a-tetrahydrocyclopenta[c]pyrane-4-carboxylic acid methylesterYield 89%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

1.63 g of the above (1S,4aS,7aR)-1-[1-(ethoxy) ethoxy]-7-[2-(hydroxy) ethyl]-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester were dissolved in dichloromethane followed by addition of 1.7 ml of pyridine and DMAP. Next, 1.0 ml of acetic anhydride were added followed by stirring for 3 hours at room temperature. The reaction mixture was then extracted with ether. After washing the organic phase with 2N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it was dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was purified by silica gel chromatography to obtain a colorless oil from the hexane-ether eluate in the form of (1S,4aS,7aR)-7-[2-(acetoxy) ethyl]-1-[1-(ethoxy) ethoxy]-1,4a,5,7a-tetrahydrocyclopenta [c] pyrane-4-carboxylic acid methylester (1.65 g, yield: 89%). The physicochemical properties of this compound are described below.

Workup

  1. extractionThe reaction mixture was then extracted with ether
  2. washAfter washing the organic phase with 2N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate and brine, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. distillationAfter distilling off the solvent under reduced pressure
  5. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-78e7d602ab494bae8b476284eefc6b41
Source dataset
uspto-grants-2001_05
Patent number
US06225478B1

Reaction notes

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