Isopropanol → Et2AlCN i-PrOH

HRID 404831Notes

Reaction equation

HRID 404831 reaction equation
C([Al])C.[CH:4]([OH:7])([CH3:6])[CH3:5].[C-:8]#[N:9].[CH2:10]([Al+:12][CH2:13][CH3:14])[CH3:11]>C1COCC1>[Al:12]([C:8]#[N:9])([CH2:13][CH3:14])[CH2:10][CH3:11].[CH3:5][CH:4]([OH:7])[CH3:6]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 16686413Diethyl aluminum cyanideHCID 16694996Ethylaluminium

Product 1

HCID 131731602Et2AlCN i-PrOH

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The sulfinimine-mediated asymmetric synthesis involves addition of ethylaluminium cyanoisopropoxide generated in situ by addition of isopropanol (i-PrOH) to diethylaluminium cyanide (Et2AlCN) to the compound VIIa. Thus treatment of compound VIIa (1.0 mmol) at −78° C. in THF with 1.5/1.0 equiv of Et2AlCN/i-PrOH gave amino nitrile VIII in good yield (50-70%).

Workup

  1. customThe sulfinimine-mediated asymmetric synthesis

Sources & evidence

ORD record
ord-868c36ae70b54fae9b68367883f5729d
Source dataset
uspto-grants-2014_06
Patent number
US08748631B2

Reaction notes

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