HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → 2-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}ethanol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | 2-((Tert-butyldimethylsilyl)oxy)acetaldehyde | HCID 4187788 | — |
| Reactant | TBAF tetrahydrofuran | HCID 11078149 | — |
| Reactant | 1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide | HCID 68380909 | — |
| Product | 2-{1-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}ethanol | HCID 67323329 | — |
Reaction Steps
The preparation is carried out starting from 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamine hydrobromide and (tertbutyldimethylsilanyloxy)acetaldehyde. The protecting group is cleaved off in THF using 5 equivalent of a 1M TBAF/THF solution: The reaction mixture was stirred at room temperature for 2 h and evaporated to dryness. The product was purified by means of reversed-phase chromatography. The fractions were extracted under basic conditions, dried, filtered and evaporated.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08907098B2 |
| Source dataset | uspto-grants-2014_12 |
| ORD ID | ord-1bfe5bac2da644279ab37adf65b6b2b7 |
| Source note | uspto-grants-2014_12 |