Octanal → HCID 66587362, compound
Reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(N(CCCC)C2CCCCC2)CCCCC1.C(=O)CCCCCCC.C1(N([CH:55]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66]CCCC)[CH:56]([O:59][CH3:60])[O:57][CH3:58])C2CCCCC2)CCCCC1>>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:55]([CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH3:66])[CH:56]([O:57][CH3:58])[O:59][CH3:60])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1Participants
Procedure
The product was prepared by above general procedure and the same chemicals except employing dibenzylamine (1a′) (98 mg, 0.5 mmol), and octanal (2c′) (96 mg, 0.75 mmol). After 24 h, the crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100) to afford the desired product 3c as a light yellowish oil (0.129 g, 70% yield); Rf=0.77 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.37-7.35 (m, 4H), 7.30-7.26 (m, 4H), 7.23-7.18 (m, 2H), 4.37-4.36 (d, J=5.03 Hz, 1H), 3.81-3.65 (m, 4H), 3.35 (s, 3H), 3.32 (s, 3H), 2.73-2.68 (m, 1H), 1.59-1.36 (m, 3H), 1.25-1.17 (m, 5H), 1.15-1.08 (m, 2H), 0.88-0.85 (t, J=7.07 Hz, 3H) ppm; 13C NMR (CDCl3, 100 MHz) δ 140.8 (C×2), 129.0 (CH×4), 128.0 (CH×4), 126.6 (CH2×2), 107.5, 57.4, 54.8, 54.5 (CH2×2), 54.3, 31.9, 29.4, 26.9, 26.5, 22.7, 14.1 ppm; FTIR (neat): v=3015, 1215, 754, 700, 494 cm−1; HRMS (ESI, m/z): calcd for C24H36NO2+ [M+H]+ 370.2746, found: 370.2743.
Workup
- customThe product was prepared by above general procedure
- customthe crude product was purified by flash column chromatography (silica gel; ethyl acetate or diethyl ether/hexane=1:100)
Sources & evidence
- ORD record
- ord-5cde523570764e98a762c15fd1e57b0b
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079824B2
Reaction notes
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