Sodium borohydride → (R)-N-[3-(2-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine

HRID 322581Notes

Reaction equation

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

Participants

Reactant 4

HCID 4311764Sodium borohydride

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

HCID 21225700Diisobutylaluminumhydride

HCID 542740043-(2-Methylphenyl)prop-2-enenitrile

Product 1

HCID 54179190(R)-N-[3-(2-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine

Procedure

In a similar fashion, 2-methylcinnamonitrile was treated with diisobutyl aluminum hydride and the intermediate aluminum-imine complex treated with (R)-1-(3-methoxyphenyl)ethylamine. The intermediate mine was treated with ethanolic sodium borohydride. Work-up and chromatography yielded (R)-N-[3-(2-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12C, as a clear, colorless oil; m/z (rel. int.) 281 (M+, 4), 266 (15), 176 (18), 146 (62), 135 (58), 131 (100), 115 (23), 105 (19), 91 (38), 77 (17).

Sources & evidence

ORD record: ord-46bf074a60504a6f9ac4ef21ddd54b1a
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

Loading…