Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Thionyl Chloride | HCID 24386 | — |
| Reactant | (R)-3-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylic acid hydrochloride | HCID 66799216 | — |
| Product | HCID 59505398 | HCID 59505398 | 89% |
Reaction Steps
SOCl2 (0.75 ml, 10.365 mmol, 2.4 eq) was added dropwise at 0° C., with stirring, to a suspension of (R)-3-amino-6-fluoro-2,3-dihydro-1H-indene-5-carboxylic acid hydrochloride (commercially available from NetChem (Order No. 573243)) (1 g, 4.319 mmol, 1 eq) in methanol (20 ml). The reaction mixture was stirred for 14 h at room temperature. When the reaction was complete according to TLC monitoring, concentration under reduced pressure was carried out and the residue was diluted with saturated sodium hydrogen carbonate solution (50 ml) and extracted with 10% methanol/dichloromethane (100 ml). The organic phase was dried over sodium sulfate and concentrated under reduced pressure. The desired product was in the form of a light-green solid. Yield: 89% (800 mg, 3.827 mmol)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08680159B2 |
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| Source dataset | uspto-grants-2014_03 |
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| ORD ID | ord-c2f007b25e824250961329446fa2afbe |
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| Source note | uspto-grants-2014_03 |
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