2-Propenenitrile, 2-methyl-3-phenyl- → HCID 53913293, compound

HRID 322587Notes

Reaction equation

HRID 322587 reaction equation
[CH3:1][C:2](=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]#[N:4].[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](=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:4][C@@H:30]([C:26]1[CH:27]=[CH:28][CH:29]=[C:24]([O:23][CH3:22])[CH:25]=1)[CH3:31]

Participants

5

Reactant 4

HCID 709712-Propenenitrile, 2-methyl-3-phenyl-HCID 4311764Sodium borohydrideHCID 7020759(R)-1-(3-Methoxyphenyl)ethylamineHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 53913293HCID 53913293, compound

Procedure

In a similar fashion, α-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-(2-methyl-3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine, 25G, as a clear, colorless oil; m/z (rel. int.) 281 (M+, 5), 266 (18), 190 (12), 146 (78), 135 (82), 131 (100), 115 (21), 105 (21), 91 (62), 77 (19).

Sources & evidence

ORD record
ord-329ee04defb54c2da1539e67958b4583
Source dataset
uspto-grants-2001_04
Patent number
US06211244B1

Reaction notes

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