HuagongsheHuagongshe Chemistry Print Report · For research reference only
Aluminium lithium hydride → (E)-3-amino-1-(4-(2-cyclohexylvinyl)thiophen-2-yl)propan-1-ol
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Aluminium lithium hydride | HCID 21226445 | — |
| Reactant | Ammonia methanol dichloromethane | HCID 21584172 | — |
| Reactant | (E)-2-(4-(2-cyclohexylvinyl)thiophen-2-yl)-2-hydroxyacetonitrile | HCID 86694599 | — |
| Reactant | Methyl 6-(cyclohexylmethoxy)picolinate | HCID 86694600 | — |
| Product | (E)-3-amino-1-(4-(2-cyclohexylvinyl)thiophen-2-yl)propan-1-ol | HCID 86694598 | — |
Reaction Steps
LiAlH4 reduction of (E)-2-(4-(2-cyclohexylvinyl)thiophen-2-yl)-2-hydroxyacetonitrile following the method used in Example 3 gave after flash chromatography purification (20%-30% 7N NH3/MeOH—CH2Cl2 gradient) Example 13 as a light yellow oil. Yield (0.44 g, 36%); 1H NMR (400 MHz, DMSO-d6) δ 7.19 (s, 1H), 7.13 (s, 1H), 6.25 (d, J=16.8 Hz, 1H), 5.98 (dd, J=16.0, 6.4 Hz, 1H), 4.84 (t, J=6.0 Hz, 1H), 2.72-2.58 (m, 2H), 2.24-2.08 (m, 1H), 1.78-1.58 (m, 7H), 1.38-1.02 (m, 5H); RP-HPLC tR=10.49 min; ESI-MS m/z 219.1.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09447078B2 |
| Source dataset | uspto-grants-2016_09 |
| ORD ID | ord-3135007f37884b0ca7337b4bca70dddd |
| Source note | uspto-grants-2016_09 |