Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (1S,4S)-4-amino-1,2,3,4-tetrahydronaphthalen-1-ol | HCID 86686682 | — |
| Reactant | HCID 86686951 | HCID 86686951 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86687049 | HCID 86687049 | — |
Reaction Steps
Intermediate B (74.0 mg, 454 μmol) was added to a mixture of NaH (60% in mineral oil, 27.2 mg, 681 μmol) in DMF (2.5 mL) at RT and stirred for 15 min. Intermediate 3b (100 mg, 454 μmol) was then added and the resulting mixture heated to 60° C. for 1 h. After cooling, the reaction was quenched with sat. aq. NH4Cl solution. The mixture was diluted with water and extracted with EtOAc. The combined organic extracts were concentrated in vacuo. The resulting residue was purified by FCC, using 0 to 10% [2M NH3 in MeOH] in DCM, to afford the title compound as an orange residue (122 mg, 74%). LCMS (Method 3): Rt 2.13 min, m/z 364 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09139584B2 |
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| Source dataset | uspto-grants-2015_09 |
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| ORD ID | ord-c48cefd4bacd4505826961577a7dfb54 |
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| Source note | uspto-grants-2015_09 |
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