Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | tert-Butanol | HCID 6386 | — |
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Chloro-1-iodo-4-methylbenzene | HCID 2757618 | — |
| Reactant | 1,2-Cyclohexanediol, (1S-trans)- | HCID 7057110 | — |
| Reactant | HCID 178517864 | HCID 178517864 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | HCID 178426226 | HCID 178426226 | — |
Reaction Steps
A mixture of (5S)-2-(trans-4-hydroxycyclohexyl)-2,7-diazaspiro[4.5]decan-1-one (20 mg, 0.00007 mol) which was prepared using procedures analogous to those described in the synthesis of example 472-a and followed by standard hydrogenation to remove the carbobenzyloxy (Cbz) protecting group and 2-chloro-1-iodo-4-methylbenzene (22.7 mg, 0.0000831 mol), potassium carbonate (20.1 mg, 0.000145 mol), copper(I) iodide (0.6 mg, 0.000003 mol), and (1S,2S)-cyclohexane-1,2-diol (16.1 mg, 0.000138 mol) in tert-butyl alcohol (1.0 mL, 0.010 mol) was heated at 100° C. for 18 h. The crude product was purified by prep-HPLC to afford the desired product. LC-MS: 377.1 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08563570B2 |
|---|
| Source dataset | uspto-grants-2013_10 |
|---|
| ORD ID | ord-51664176d7554bc2a46926772c8334ea |
|---|
| Source note | uspto-grants-2013_10 |
|---|
