Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol | HCID 86686674 | — |
| Reactant | HCID 86686948 | HCID 86686948 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86686949 | HCID 86686949 | 43% |
Reaction Steps
Intermediate A (180 mg, 1.11 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 133 mg, 3.33 mmol) in DMF (5 mL). The reaction was stirred for 20 min, then Intermediate 2b (310 mg, 1.11 mmol) was added in DMF (5 mL) and the resulting mixture heated to 60° C. for 3 h. After cooling, the reaction was quenched by dropwise addition of MeOH. The solution was loaded onto an SCX-2 cartridge, which was washed with MeOH and product eluted with 2M NH3 in MeOH. The residue was purified by FCC, using 2-20% [2M NH3 in MeOH] in DCM, to give the title compound (200 mg, 0.47 mmol, 43%). LCMS (Method 4): Rt 0.28 min, m/z 407 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09145413B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-ea4a709732e147598afae4ccfa5a664b |
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| Source note | uspto-grants-2015_09 |
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