HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ammonia → (1S,3S,4R)-4-Bromo-3-hydroxycyclohexanecarboxylic amide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ammonia | HCID 222 | — |
| Reactant | Methanol | HCID 887 | — |
| Reactant | (1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one | HCID 10878278 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | (1S,3S,4R)-4-Bromo-3-hydroxycyclohexanecarboxylic amide | HCID 69375303 | — |
Reaction Steps
(1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one (352a) (2.88 g, 14.0 mmol) was taken up in THF (27 mL) and treated with 0.880 ammonia (7.1 mL) at 20° C. for 24 h with stirring. The solvent was then removed in vacuo to give a white solid in quantitative yield; [α]D=−55.4° (c=1, MeOH).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07141564B2 |
| Source dataset | uspto-grants-2006_11 |
| ORD ID | ord-29699c1d13014cd09ede5b0449092600 |
| Source note | uspto-grants-2006_11 |