Sodium borohydride → [1-(6-Tert-butyl-4-methylpyridin-3-yl)ethyl]amine

HRID 1919837Notes

Reaction equation

HRID 1919837 reaction equation
[C:1]([C:5]1[CH:12]=[C:11]([CH3:13])[C:8]([C:9]#[N:10])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C[Mg+].[Br-].[C:17]1(C)C=CC=CC=1.C1COCC1.[BH4-].[Na+]>>[C:1]([C:5]1[N:6]=[CH:7][C:8]([CH:9]([NH2:10])[CH3:17])=[C:11]([CH3:13])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 4311764Sodium borohydrideHCID 22635083Tetrahydrofuran tolueneHCID 534188646-Tert-butyl-4-methylnicotinonitrile2×HCID 178418689HCID 178418689, compound

Product 1

HCID 67501210[1-(6-Tert-butyl-4-methylpyridin-3-yl)ethyl]amine

Procedure

The title compound was synthesized according to the procedure described for the synthesis of [1-(6-tert-butylpyridin-3-yl)ethyl]amines starting from 6-tert-butyl-4-methylnicotinonitrile (intermediate 24) (250 mg, 1.43 mmol), MeMgBr 1.4 M 75/25 toluene/THF (2.55 ml, 3.58 mmol) and NaBH4 (135 mg, 3.58 mmol). Purified by normal phase chromatography with 15 to 20% MeOH/CH2Cl2. (Yield 55 mg, 20%). 1H NMR (400 MHz, CDCl3) δ ppm 1.34 (s, 9 H) 1.42 (d, J=6.64 Hz, 3 H) 2.35 (s, 3 H) 4.34 (q, J=6.64 Hz, 1 H) 7.07 (s, 1 H) 8.60 (s, 1 H).

Workup

  1. customPurified by normal phase chromatography with 15 to 20% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-d54be2799ad64ac09e852c4361960bf4
Source dataset
uspto-grants-2012_05
Patent number
US08168668B2

Reaction notes

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