HCID 11084286, compound → HCID 86755226, compound

HRID 1637037Notes

Reaction equation

HRID 1637037 reaction equation
[CH2:1]([NH:7][C@@H:8]([CH3:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[CH:2]=[CH:3]/[CH:4]=[CH:5]/[CH3:6].C([Li])CCC.[C:21]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])(=[O:27])/[CH:22]=[CH:23]/[CH:24]=[CH:25]/[CH3:26]>>[CH2:1]([N:7]([C@@H:8]([CH3:15])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[C@@H:23]([CH:24]=[CH:25][CH3:26])[CH2:22][C:21]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH3:6]

Participants

4

Reactant 3

HCID 11084286HCID 11084286, compoundHCID 86755222HCID 86755222, compoundHCID 178418339Butyllithium

Product 1

HCID 86755226HCID 86755226, compoundYield 128.9%

Procedure

(S)-(E,E)-N-Hexa-2,4-dienyl-α-methylbenzylamine (3) (0.500 g, 2.49 mmol), 1.6M butyllithium (1.35 ml, 2.16 mmol) and t-butyl sorbate (11) (0.279 g, 1.66 mmol) were reacted according the procedure of Example 1. Flash chromatography of the product on silica gel [ethyl acetate/petroleum ether (1:19)] afforded the title compound as a colourless oil (0.791 g, 72%). δH (200 MHz; CDCl3) 7.39-7.18 (5H, m, Ph), 6.12-5.93 (2H, m, CH=CH--CH=CH), 5.69-5.41 (4H, m, CH3CH=CH and CH=CH--CH=CH), 4.0 (1H, q, J=6.8, PhCHCH3), 3.87-3.75 (1H, m, CH3CH=CHCH), 3.21-3.09 (2H, m, NCH2), 2.40 (1H, dd, J=14.1 and 6.4, CH2CO2), 2.25 (1H, dd, J=14.1 and 8.5, CH2CO2), 1.76-1.71 (6H, m, CH3CH=CHCH and CH=CHCH3), 1.41 (9H, s, (CH3)3C), 1.37 (3H, d, J=6.7, PhCHCH3).

Sources & evidence

ORD record
ord-7de919343e6c4f72a33660ed33970b1b
Source dataset
uspto-grants-2000_03
Patent number
US06037498

Reaction notes

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