HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → HCID 117729265, compound
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 117728921 | HCID 117728921 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 117729265 | HCID 117729265 | 96.3% |
Reaction Steps
A suspension of sodium hydride (60% dispersion in oil, 548 mg, 14.6 mmol) in dry DMF (10.0 mL) under nitrogen was treated with Intermediate 1 (800 mg, 4.9 mmol) and the mixture was stirred for 20 min. Intermediate 38c (1.28 g, 4.6 mmol) was added and the mixture was stirred at RT for 4 hours then quenched with MeOH. The mixture was further diluted with MeOH and applied to a pre-conditioned (MeOH) SCX-2 cartridge (25 g). The cartridge was eluted with MeOH then 2M NH3 in MeOH. The relevant product containing fractions were combined and concentrated in vacuo to give the title compound as a dark brown oil (1.8 g, 86%). LCMS (Method 3): Rt 0.6, m/z 407 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09359354B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-cf44b35770ba4130ab80948b2cbcc079 |
| Source note | uspto-grants-2016_06 |