Sodium borohydride → HCID 54282868, compound

HRID 322585Notes

Reaction equation

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

Participants

Reactant 4

HCID 4311764Sodium borohydride

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

HCID 21225700Diisobutylaluminumhydride

HCID 542355653-(3-Methylphenyl)-2-propenenitrile

Product 1

HCID 54282868HCID 54282868, compound

Procedure

In a similar fashion, 3-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-(3-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12G, as a clear, colorless oil; m/z (rel. int.) 281 (M+, 5), 266 (9), 176 (24), 146 (71), 135 (62), 131 (100), 115 (23), 105 (19), 91 (41), 77 (18).

Sources & evidence

ORD record: ord-15df5bc1c9924190a1e1528e61b93c9d
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

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