3-Phenylprop-2-enenitrile → HCID 54421245, compound

HRID 322586Notes

Reaction equation

[C:1](#[N:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H-].C([Al+]CC(C)C)C(C)C.[CH3:21][O:22][C:23]1[CH:24]=[C:25]([C@H:29](N)[CH3:30])[CH:26]=[CH:27][CH:28]=1.[BH4-].[Na+]>>[C:4]1([CH:3]=[CH:2][CH2:1][NH:10][C@@H:29]([C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([O:22][CH3:21])[CH:24]=2)[CH3:30])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 4

HCID 746673-Phenylprop-2-enenitrile

HCID 4311764Sodium borohydride

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

HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 54421245HCID 54421245, compound

Procedure

In a similar fashion, cinnamonitrile 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-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine, 25E, as a clear colorless oil; m/z (rel. int.) 267 (M+. 3), 252 (14),176 (17), 135 (62),117 (100), 105 (28), 91 (56), 77 (33).

Sources & evidence

ORD record: ord-318ac4f5dbff4905b45da8985900cf0b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

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