Sodium borohydride → [1-(6-Tert-butyl-2-methylpyridin-3-yl)ethyl]amine

HRID 1919841Notes

Reaction equation

HRID 1919841 reaction equation
[C:1](C1C=CC(C#N)=CN=1)(C)(C)C.[C:13]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([CH3:25])[N:18]=1)([CH3:16])([CH3:15])[CH3:14].C[Mg+].[Br-].C1(C)C=CC=CC=1.C1COCC1.[BH4-].[Na+]>>[C:13]([C:17]1[N:18]=[C:19]([CH3:25])[C:20]([CH:21]([NH2:22])[CH3:1])=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

6

Reactant 5

HCID 4311764Sodium borohydrideHCID 194251856-Tert-butylpyridine-3-carbonitrileHCID 22635083Tetrahydrofuran tolueneHCID 579390166-Tert-butyl-2-methylnicotinonitrile2×HCID 178418689HCID 178418689, compound

Product 1

HCID 57939020[1-(6-Tert-butyl-2-methylpyridin-3-yl)ethyl]amine

Procedure

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).

Workup

  1. customPurified by normal phase chromatography with 20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-071abe6757f8480eafbbbbf0687fbb44
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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