Dibenzylamine → HCID 66586829, 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.[O:33]=CCCCC(OC)=O.[C:42]([O:45][CH2:46][CH2:47][CH2:48][CH:49](N(C1CCCCC1)C1CCCCC1)[CH:50]([O:53][CH3:54])[O:51][CH3:52])(=O)C>>[CH2:9]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH:49]([CH:50]([O:53][CH3:54])[O:51][CH3:52])[CH2:48][CH2:47][C:46]([O:45][CH3:42])=[O:33])[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 methyl 5-oxopentanoate (2h′) (97 mg, 0.75 mmol). After 48 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 3h as a light yellowish oil (0.124g, 67% yield); Rf=0.54 (hexane:ethyl acetate=3:1); 1H NMR (CDCl3, 400 MHz) δ 7.33-7.27 (m, 8H), 7.25-7.19 (m, 2H), 4.44-4.42 (d, J=5.53 Hz, 1H), 3.82-3.63 (m, 4H), 3.55 (s, 3H), 3.363-3.359 (m, 6H), 2.78-2.73 (m, 1H), 2.53-2.26 (m, 2H), 1.86-1.70 (m, 2H) ppm; 13C NMR (CDCl3, 100 MHz) δ 174.2, 140.2 (C×2), 129.1 (CH×4), 128.1 (CH×4), 126.8 (CH2×2), 106.7, 56.6, 54.8, 54.2 (CH2×2), 53.6, 51.3, 31.1, 21.9 ppm; FTIR (neat): v=3017, 1454, 1215, 758, 494 cm−1; HRMS (ESI, m/z): calcd for C22H30NO4+ [M+H]+ 372.2175, found: 372.2178.
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-0d6fc662bf664fdd9fc966fb940091af
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079824B2
Reaction notes
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