Sodium borohydride → HCID 53838794, compound

HRID 322582Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:3]=1[CH:4]=[CH:5][C:6]#[N:7].[H-].C([Al+]CC(C)C)C(C)C.[CH3:24][O:25][C:26]1[CH:27]=[C:28]([C@H:32](N)[CH3:33])[CH:29]=[CH:30][CH:31]=1.[BH4-].[Na+]>>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH3:13])[C:3]=1[CH:4]=[CH:5][CH2:6][NH:7][C@@H:32]([C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([O:25][CH3:24])[CH:27]=1)[CH3:33]

Participants

Reactant 4

HCID 4311764Sodium borohydride

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

HCID 21225700Diisobutylaluminumhydride

HCID 54347343HCID 54347343, compound

Product 1

HCID 53838794HCID 53838794, compound

Procedure

In a similar fashion, 2,4,6-trimethylcinnamonitrile 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-(2,4,6-trimethylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12D, as a clear, colorless oil; m/z (rel. int.) 309 (M+, 8), 294 (25), 174 (82), 159 (100), 135 (52), 129 (29), 105 (21), 91 (17), 77 (14).

Sources & evidence

ORD record: ord-31a0bd2eac7c4387ba347276f9722f1f
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

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