HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Hydroxide → (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2,2,2-Trifluoro-N-((1S,4R)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide | HCID 86686672 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Methanol--water (1/1) | HCID 22242641 | — |
| Product | Ammonia | HCID 222 | — |
| Product | (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol | HCID 86686674 | 200% |
Reaction Steps
Sodium hydroxide (2.10 g, 53.0 mmol) was added to an ice cold solution of Intermediate 1c (3.43 g, 13.2 mmol) in MeOH/water (2:1, 50 mL) and stirred for 3.5 h. The mixture was loaded on to a SCX-2 cartridge, eluting with MeOH then 2M NH3 in MeOH, to yield the title compound (2.30 g, 13.2 mmol, 99%). 1H NMR (400 MHz, d6-DMSO): 1.66-1.90 (4H, m), 3.71-3.77 (1H, t, J 5.4 Hz), 4.46-4.54 (1H, t, J 5.4 Hz), 7.14-7.22 (2H, m), 7.32-7.38 (1H, m), 7.40-7.46 (1H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09029373B2 |
| Source dataset | uspto-grants-2015_05 |
| ORD ID | ord-857d8c6557c449d9adcae4e533a06be1 |
| Source note | uspto-grants-2015_05 |