1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)- synthesis
- Product Name:1H-Azepino(5,4,3-cd)indole, 3,4,5,6-tetrahydro-6-(2-methyl-1-propenyl) -, (-)-
- CAS Number:80152-02-9
- Molecular formula:C15H18N2
- Molecular Weight:226.32
![1H-Pyrrolo[4,3,2-ef][2]benzazepine-1-carboxylic acid, 3,4,5,6-tetrahydro-6-(2-methyl-1-propen-1-yl)-, 1,1-dimethylethyl ester, (6R)-](/CAS/20210305/GIF/1255909-60-4.gif)
1255909-60-4
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Yield:80152-02-9 90%
Reaction Conditions:
with water;potassium carbonate in methanol at 100;Inert atmosphere;
Steps:
Ent-14 (10 mg, 0.031 mmol)was dissolved in MeOH (1.0 mL) and water (0.3 mL). K2CO3 (12mg, 0.093 mmol) was added and the mixture was stirred overnight at100°C. The reactionwas cooled to room temperature, extracted with EtOAc (50 mL), washed with water (5 mL) and brine (5 mL), dried andconcentrated, purified by silica gel column chromatography (DCM/MeOH 25:1) to give (-)-aurantioclavine (6 mg, 90%) as a colorless oil: [a]22D = -37 (c = 0.33, CHCl3),[lit.2 [a]D = -34 (c = 1.25,CHCl3)], [Its antipode (+)-aurantioclavine (ent-1) (6 mg, 90%) can also beprepared from 14 (10 mg, 0.031 mmol) asthe same procedure described above as acolorless oil: [a]27D = +45 (c = 0.30, CHCl3)];1H NMR(400 MHz, CDCl3) d 8.27 (br s, 1H), 7.29 - 7.18 (m, 1H), 7.09 (t, J= 7.6 Hz, 1H), 6.98 (s, 1H), 6.82 (d, J = 7.6 Hz, 1H), 5.44 (d, J= 8.8 Hz, 1H), 4.93 (d, J = 8.8 Hz, 1H), 3.57 (m, 1H), 3.21 - 2.93 (m, 3H),2.71 (br s, 1H), 1.84 (s, 6H); 13C NMR (100 MHz, CDCl3) d 137.3,137.0, 134.1, 126.8, 125.2, 121.5, 121.1, 117.9, 115.2, 109.4, 62.4, 48.6, 30.2,25.8, 18.3.
References:
Lei, Ting;Zhang, Hongbin;Yang, Yu-Rong [Tetrahedron Letters,2015,vol. 56,# 43,p. 5933 - 5936] Location in patent:supporting information
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