Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | HCID 68646726 | HCID 68646726 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Oxolane--water (1/1) | HCID 21881883 | — |
| Product | HCID 3687912 | HCID 3687912 | 65.3% |
Reaction Steps
107.2 (3RS,4SR)-4-Trifluoromethyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (9.76 g) was dissolved in THF/water (1:1 10 ml) and LiOH (0.826 g) was added to the emulsion. The mixture was stirred for 18 h at 25° C. The reaction mixture was then diluted with CH2Cl2 (50 ml) and treated with HCl (1N, 20 ml). The aqueous phase was extracted twice with CH2Cl2 (20 ml) and the combined organic layers were dried over Na2SO4, filtered and evaporated to dryness to yield (3RS,4SR)-4-trifluoromethyl-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (5.8 g) as light yellow solid. MS 284.3 ([M+H]+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07820699B2 |
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| Source dataset | uspto-grants-2010_10 |
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| ORD ID | ord-dc55f9d456024f958e4f95c42e2a8077 |
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| Source note | uspto-grants-2010_10 |
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