HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | Sodium cyanoborohydride | HCID 5003444 | — |
| Reactant | 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol | HCID 21966601 | — |
| Solvent | Trifluoroacetic acid acetate | HCID 23437676 | — |
| Product | 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol | HCID 21966615 | 73% |
Reaction Steps
A solution of 109 mg (0.5 mmol) 5-(6-Fluoro-1H-indol-5-yl)-pent-4-yn-1-ol in 3 ml AcOH/TFA 2:1 was cooled to 0° C., treated with NaCNBH3 and stirred for 1 hour at room temperature. The mixture was poured into icy water, made strongly alkaline by the addition of 2M NaOH, and extracted with EtOAc. Drying of the combined organic layers with MgSO4, evaporation of the solvent, and chromatography on silica gel with CH2Cl2/MeOH 49:1 gave 80 mg (73%) of 5-(6-Fluoro-2,3-dihydro-1H-indol-5-yl)-pent-4-yn-1-ol as a colorless oil, MS: 220 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06706751B2 |
| Source dataset | uspto-grants-2004_03 |
| ORD ID | ord-328b44220787472e859ca24153de000b |
| Source note | uspto-grants-2004_03 |