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 86686976 | HCID 86686976 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86686977 | HCID 86686977 | 72% |
Reaction Steps
Intermediate A (150 mg, 0.92 mmol) was added to a suspension of sodium hydride (60% in mineral oil, 147 mg, 3.66 mmol) in DMF (3.0 mL). The reaction was stirred for 20 min, then Intermediate 17a (280 mg) in DMF (3.0 mL) was added and the reaction heated to 60° C. for 90 min. The mixture was cooled and quenched by dropwise addition of MeOH. The solution was diluted with MeOH and loaded onto an SCX-2 cartridge, which was washed sequentially with MeOH and 2M NH3 in MeOH. The basic fractions were evaporated in vacuo then purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound (234 mg, 0.66 mmol, 72%). LCMS (Method 4): Rt 1.60 min, m/z 354 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08907094B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-38803b7bdaee4402ba6ca884a02cf80a |
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| Source note | uspto-grants-2014_12 |
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