HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium borohydride → [1-(6-Tert-butyl-2-methylpyridin-3-yl)ethyl]amine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium borohydride | HCID 4311764 | — |
| Reactant | 6-Tert-butylpyridine-3-carbonitrile | HCID 19425185 | — |
| Reactant | Tetrahydrofuran toluene | HCID 22635083 | — |
| Reactant | 6-Tert-butyl-2-methylnicotinonitrile | HCID 57939016 | — |
| Reactant | HCID 178418689 | HCID 178418689 | — |
| Product | [1-(6-Tert-butyl-2-methylpyridin-3-yl)ethyl]amine | HCID 57939020 | — |
Reaction Steps
The title compound was synthesized according to the procedure described for the synthesis of 6-tert-butylnicotinonitrile starting from 6-tert-butyl-2-methylnicotinonitrile (intermediate 31) (100 mg, 0.57 mmol), used crude from the above described description; MeMgBr 1.4 M 75/25 toluene/THF (1.4 ml, 1.4 mmol) and NaBH4 (55 mg, 1.4 mmol). Purified by normal phase chromatography with 20% MeOH/CH2Cl2. (Yield 31.5 mg, 29%). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.34 (s, 9 H), 1.36 (d, J=6.64 Hz, 3 H), 2.56 (s, 3H), 4.32-4.40 (m, 1 H), 7.15-7.19 (m, J=8.20 Hz, 1 H), 7.68 (d, J=8.20 Hz, 1 H).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08168668B2 |
| Source dataset | uspto-grants-2012_05 |
| ORD ID | ord-071abe6757f8480eafbbbbf0687fbb44 |
| Source note | uspto-grants-2012_05 |