Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol | HCID 86686674 | — |
| Reactant | HCID 86687003 | HCID 86687003 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 86687004 | HCID 86687004 | 28% |
Reaction Steps
To a solution of Intermediate A (50 mg, 0.309 mmol) in DMF (2 mL) was added NaH (60% in oil, 33 mg, 0.80 mmol) and the mixture stirred at RT for 20 min, before Intermediate 28b (110 mg, 0.280 mmol) was added. This mixture was heated at 60° C. in the microwave for 1.25 h. The reaction mixture was applied to an SCX-2 cartridge (25 g) and washed with MeOH. The product was eluted with 2M NH3 in MeOH; concentration in vacuo gave a residue. FCC, using 0-7% [2M NH3 in MeOH] in DCM gave the title compound as a viscous yellow oil (42 mg, 28%). LCMS (Method 4): Rt 2.55 min, m/z 536 [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-e9db0e4093954fc8a00b24ba87a7c192 |
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| Source note | uspto-grants-2015_09 |
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