Trifluoroacetic acid → 1'-pentyl-6,7-dihydro-5H-spiro[1,3-dioxolo[4,5-g]isoquinoline-8,3'-indole]-2',5(1'H)-dione
Reaction equation
[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:25]3[C:17](=[CH:18][C:19]4[O:20][CH2:21][O:22][C:23]=4[CH:24]=3)[C:16](=[O:26])[CH2:15]2)[C:7]1=[O:27])[CH2:2][CH2:3][CH2:4][CH3:5].[N-:28]=[N+]=[N-].[Na+].FC(F)(F)C(O)=O>O>[CH2:1]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]2([C:25]3[CH:24]=[C:23]4[O:22][CH2:21][O:20][C:19]4=[CH:18][C:17]=3[C:16](=[O:26])[NH:28][CH2:15]2)[C:7]1=[O:27])[CH2:2][CH2:3][CH2:4][CH3:5]Participants
Conditions
- Temperature
- 50 °C
Procedure
A mixture of 1′-pentylspiro[indeno[5,6-d][1,3]dioxole-5,3′-indole]-2′,7(1′H,6H)-dione (0.10 g, 0.28 mmol), sodium azide (0.09 g, 1.40 mmol) and trifluoroacetic acid (2.00 mL) was stirred at 50° C. overnight. The mixture was poured into water (100 mL) and extracted with ethyl acetate (100 mL). The organic layer was washed with water, dried over sodium sulfate and filtered. The filtrate was concentrated in vacuo to dryness. The residue was subjected to flash column chromatography to afford the title compound (0.08 g, 74%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.60 (s, 1H), 7.30 (td, 1H), 7.20 (dd, 1H), 6.98 (td, 1H), 6.93 (d, 1H), 6.32 (br, 1H), 6.21 (s, 1H), 5.97-5.92 (m, 2H), 4.02 (dd, 1H), 3.87-3.70 (m, 2H), 3.47 (dd, 1H), 1.80-1.66 (m, 2H), 1.42-4.30 (m, 4H), 0.90 (t, 3H); 13C NMR (75 MHz, CDCl3) δ 175.8, 165.2, 151.6, 147.9, 141.7, 134.3, 130.9, 129.0, 124.5, 123.2, 122.9, 109.0, 108.5, 105.4, 101.9, 51.9, 48.2, 40.4, 29.1, 27.1, 22.3, 14.0; MS (ES+) m/z 379.3 (M+1).
Workup
- extractionextracted with ethyl acetate (100 mL)
- washThe organic layer was washed with water
- dry with materialdried over sodium sulfate
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo to dryness
Sources & evidence
- ORD record
- ord-64ab6f2d8e3f429db48e77906d0d1c7d
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08106087B2
Reaction notes
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