HCID 18913423, compound → HCID 59200452, compound

HRID 1685302Notes

Reaction equation

HRID 1685302 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([CH3:11])[C:9]#[N:10]>C1COCC1>[NH2:10][CH2:9][C:8]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)([OH:7])[CH3:11]

Participants

4

Reactant 2

HCID 18913423HCID 18913423, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 59200452HCID 59200452, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a cool (0° C.), stirring solution of LiAlH4 (57 mg, 1.502 mmol) in THF (5 mL) was added dropwise via cannula a solution of 2-hydroxy-2-(pyridin-2-yl)propanenitrile (92 mg, 0.621 mmol) in THF (5 mL). After 1 h at 0° C., powdered Na2SO4.10H2O was added and the reaction was allowed to warm to RT until the colour dissipated. The solid was removed by filtration. The filtrate was concentrated to afford the product (65 mg) as an oil: 1H NMR (400 MHz, MeOD) δ ppm: 8.44 (1H, d, J=4.04 Hz), 7.76-7.86 (1H, m), 7.69 (1H, d, J=8.08 Hz), 7.21-7.30 (1H, m), 3.04 (1H, d, J=13.39 Hz), 2.86 (1H, d, J=13.14 Hz), 1.39 (3H, s).

Workup

  1. temperatureto warm to RT until the colour
  2. customThe solid was removed by filtration
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-92947ef638224e43b58eb5560400eea0
Source dataset
uspto-grants-2012_04
Patent number
US08148400B2

Reaction notes

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