Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Lithium borohydride | HCID 4148881 | — |
| Reactant | HCID 67270240 | HCID 67270240 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 67270361 | HCID 67270361 | 97.1% |
Reaction Steps
To a solution of tert-butyl (2S,4S)-4-{[(1-isopropyl-1H-indazol-3-yl)carbonyl]amino}-2-(2-methoxy-2-oxoethyl)pyrrolidine-1-carboxylate (200 mg, 0.45 mmol, step 5 of Example 9) in tetrahydrofuran (5 mL) was added lithium borohydride solution (2 M in tetrahydrofuran, 1.13 mL, 2.25 mmol) at room temperature. The mixture was stirred at room temperature for 20 h. To the resulting mixture water (10 mL) was added. The mixture was extracted with ethyl acetate (100 mL). The organic layer was washed with brine (10 mL). The organic layer was separated, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:1) to give 182 mg (97%) of the title compound as a white amorphous solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07906532B2 |
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| Source dataset | uspto-grants-2011_03 |
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| ORD ID | ord-9b683e6f01734d8ba98bb1d85e3ec516 |
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| Source note | uspto-grants-2011_03 |
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