3-(4-Methylphenyl)prop-2-enenitrile → (R)-N-[3-(4-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine

HRID 322580Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][C:8]#[N:9])=[CH:4][CH:3]=1.[H-].C([Al+]CC(C)C)C(C)C.[CH3:22][O:23][C:24]1[CH:25]=[C:26]([C@H:30](N)[CH3:31])[CH:27]=[CH:28][CH:29]=1.[BH4-].[Na+]>>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH:6]=[CH:7][CH2:8][NH:9][C@@H:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=2)[CH3:31])=[CH:4][CH:3]=1

Participants

Reactant 4

HCID 342423-(4-Methylphenyl)prop-2-enenitrile

HCID 4311764Sodium borohydride

HCID 7020759(R)-1-(3-Methoxyphenyl)ethylamine

HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 54239855(R)-N-[3-(4-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine

Procedure

In a similar fashion, 4-methylcinnamonitrile was treated with diisobutyl aluminum hydride and the intermediate aluminum-imine complex treated with (R)-1-(3-methoxyphenyl)ethylamine. The intermediate imine was treated with ethanolic sodium borohydride. Work-up and chromatography yielded (R)-N-[3-(4-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12B, as a clear, colorless oil; m/z (rel. int.) 281 (M+, 6), 266 (5), 176 (27), 146 (75), 135 (63), 131 (100), 115 (25), 105 (21), 91 (21), 77 (21).

Sources & evidence

ORD record: ord-0a0359fa9a764fdfb8741baf1ba277df
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

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