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

HRID 253518Notes

Reaction equation

HRID 253518 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-e54f2cb9199f4d32b319a99355c5a3ff
Source dataset
uspto-grants-2011_01
Patent number
US07872045B2

Reaction notes

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