Sodium borohydride → HCID 53750765, compound

HRID 322583Notes

Reaction equation

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

Participants

Reactant 4

HCID 4311764Sodium borohydride

HCID 43190584-Isopropylcinnamonitrile

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

HCID 21225700Diisobutylaluminumhydride

Product 1

HCID 53750765HCID 53750765, compound

Procedure

In a similar fashion, 4-isopropylcinnamonitrile 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-(4-isopropylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12E, as a clear, colorless oil; m/z (rel. int.) 309 (M+, 9), 294 (7),174 (98),159 (22),135 (80), 117 (100),105 (35), 91 (37), 77 (19).

Sources & evidence

ORD record: ord-4f0a096359be4b398f06ceff127c9e8b
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06211244B1

Reaction notes

Loading…