1-Hexadecene → HCID 58460764, compound
Reaction equation
[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:2]=[CH2:3].[CH2:12]=[CH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25]CC>>[CH2:1]([NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])/[CH:2]=[CH:3]\[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH3:12]Participants
Procedure
Following the allylic amide CM general procedure, tert-butyl allylcarbamate (4.40 mg, 0.0280 mmol) was treated with 1-hexadecene (64.5 mg, 0.290 mmol), 5.0 mol % of in situ-generated complex 2 (75.0 μL, 0.02 M, 1.50 μmol), and allowed to stir under vacuum for 1 h. Z-selectivity could not be determined from 400 MHz 1H NMR spectrum of unpurified product. The resulting brown oil was purified by silica gel chromatography (96:2:2 hexanes:EtOAc:CH2Cl2) to afford 19f (8.30 mg, 0.0230 mmol, 84.0% yield, 81% Z isomer) as a white, crystalline solid. M.P. 42-46° C.; IR (neat): 3353 (br), 2922 (s), 2853 (s), 1700 (s), 1501 (m), 1457 (m), 1390 (m), 1365 (m), 1247 (m), 1170 (s), 1046 (w), 1023 (w); 1H NMR (400 MHz, CDCI3): 5.60-5.34 (overlapping Z/E 2H, m), 4.45 (overlapping Z/E, 1H, br d, J=15.6 Hz), 3.74 (E, 1H, br s), 3.66 (Z, 1H, br s), 2.06-1.96 (overlapping Z/E, 2H, m), 1.43 (overlapping Z/E, 9H, s), 1.41-1.24 (overlapping Z/E, 24H, m), 0.86 (overlapping Z/E, 3H, t, J=7.8 Hz); 13C NMR (100 MHz, CDCl3): 156.0, 155.9, 133.4, 126.3, 125.9, 79.4, 77.4, 32.4, 32.1, 29.9, 29.8 29.8, 29.8, 29.7, 29.7, 29.5, 29.4, 29.3, 28.6, 27.5, 22.8, 19.2, 14.3; HRMS (ESI+) [M+Na]+ calcd for C22H43NO2Na: 376.3191, found: 376.3184.
Workup
- customThe resulting brown oil was purified by silica gel chromatography (96:2:2 hexanes:EtOAc:CH2Cl2)
Sources & evidence
- ORD record
- ord-6a9fc6e0d20a47b4888069d58fc85d7b
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598400B2
Reaction notes
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