(4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-one → [3-[(R)-3-(tert-Butyldimethylsilanyloxy)-5-oxocyclopent-1-enylsulfanyl]propylsulfanyl}acetic acid methyl ester

HRID 1862487Notes

Reaction equation

HRID 1862487 reaction equation
[Si:1]([O:8][CH:9]1[CH:14]2[C@@H:12](O2)[C:11](=[O:15])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:16][O:17][C:18](=[O:25])[CH2:19][S:20][CH2:21][CH2:22][CH2:23][SH:24].[Si](O[C@@H]1CC(=O)C=C1)(C(C)(C)C)(C)C>C(Cl)Cl>[CH3:16][O:17][C:18](=[O:25])[CH2:19][S:20][CH2:21][CH2:22][CH2:23][S:24][C:12]1[C:11](=[O:15])[CH2:10][C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH:14]=1

Participants

5

Reactant 3

HCID 2734530(4R)-(+)-t-Butyldimethylsiloxy-2-cyclopenten-1-oneHCID 15406174Methyl [(3-sulfanylpropyl)sulfanyl]acetateHCID 86587272(R)-4-(tert-Butyldimethylsilanyloxy)-6-oxabicyclo[3.1.0]hexan-2-one

Product 1

HCID 15406175[3-[(R)-3-(tert-Butyldimethylsilanyloxy)-5-oxocyclopent-1-enylsulfanyl]propylsulfanyl}acetic acid methyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The epoxide 3 prepared above was diluted with CH2Cl2 (30 mL), (3-mercaptopropylsulfanyl) acetic acid methyl ester 4 (1.93 g, 10.7 mmol), prepared according to Chem. Pharm. Bull. 28 (2), 1980, 558-566, was added and the solution was cooled to 0° C. Basic alumina (11.9 g) was added and the reaction mixture was warmed to room temperature. After stirring for 18 h the mixture was filtered through celite and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel, 6:1 hex/EtOAc) to yield 3.6 g (80%) of the above titled compound.

Workup

  1. customprepared
  2. additionBasic alumina (11.9 g) was added
  3. temperaturethe reaction mixture was warmed to room temperature
  4. filtrationwas filtered through celite and
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 6:1 hex/EtOAc)

Sources & evidence

ORD record
ord-2fa87da22b2243b1982fcc59a5d0c3d2
Source dataset
uspto-grants-2003_03
Patent number
US06538018B1

Reaction notes

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