Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Phosphate | HCID 1061 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Methanesulfonyl chloride | HCID 31297 | — |
| Reactant | HCID 57233113 | HCID 57233113 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 88444072 | HCID 88444072 | 96.4% |
Reaction Steps
At 0° C., methanesulfonyl chloride (0.20 ml, 2.6 mmoles) was added to a solution of (1S, 2S, 3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentanol (1.08 g, 1.73 mmoles) and triethylamine (0.44 ml, 3.2 mmoles) in methylene chloride (9 ml). After stirring the mixture at 0° C. for 15 minutes, 0.2M phosphate buffer (pH 7.0) was added to the reaction mixture and the mixture was subjected to extraction with ethyl ether. The ether extract solution was dried on anhydrous sodium sulfate and then the solvent was distilled off. The residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:9, v/v) to obtain (1S,2S,3S)-2,3-bis-(t-butyldiphenylsilyloxymethyl)-1-cyclopentyl methanesulfonate (1.169 g, Yield 96%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05374625 |
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| Source dataset | uspto-grants-1994_12 |
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| ORD ID | ord-2b5d3d2f9e404fbc9d652bebb51c0a28 |
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| Source note | uspto-grants-1994_12 |
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