Sodium borohydride → HCID 53864029, compound

HRID 322584Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[CH:4]=[CH:5][C:6]#[N:7].[H-].C([Al+]CC(C)C)C(C)C.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C@H:31](N)[CH3:32])[CH:28]=[CH:29][CH:30]=1.[BH4-].[Na+]>>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[CH:4]=[CH:5][CH2:6][NH:7][C@@H:31]([C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([O:24][CH3:23])[CH:26]=1)[CH3:32]

Participants

Reactant 4

HCID 4311764Sodium borohydride

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

HCID 21225700Diisobutylaluminumhydride

HCID 54306872HCID 54306872, compound

Product 1

HCID 53864029HCID 53864029, compound

Procedure

In a similar fashion, 2,4-dimethylcinnamonitrile 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-(2,4-dimethylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12F, as a clear, colorless oil; m/z (rel. int.) 295 (M+, 8), 294 (15), 174 (29), 160 (75), 145 (100), 135 (68), 117 (21), 105 (30), 91 (26), 77 (19).

Sources & evidence

ORD record: ord-276488c672dc465797ed7a57866b82a8
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

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