Facile and efficient way to synthesize the radical cyclization precursor methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3-oxo-2- (phenylseleno)propanoate for kinetic research

Article abstract of DOI:10.1080/00397910600977574

Methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-3- oxo-2-(phenylseleno)propanoate was prepared in 10 steps in good to excellent yield using benzophenone and hydrazine hydrate as the starting materials. Copyright Taylor & Francis Group, LLC.

Full text of DOI:10.1080/00397910600977574

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Facile and Efficient Way to Synthesize
the Radical Cyclization Precursor Methyl
3‐(tert‐Butyl((E)‐3‐(2,2‐diphenylcyclopropyl)‐2‐pr
for Kinetic Research
Jindi Yu a , Gaoyan Lian a & Danwei Zhang a
a Department of Chemistry, Fudan University, Shanghai, China
Version of record first published: 25 Jul 2007
To cite this article: Jindi Yu, Gaoyan Lian & Danwei Zhang (2007): Facile
and Efficient Way to Synthesize the Radical Cyclization Precursor Methyl
3‐(tert‐Butyl((E)‐3‐(2,2‐diphenylcyclopropyl)‐2‐propenyl)amino)‐3‐Oxo‐2‐(phenylseleno)propanoate for Kinetic
Research, Synthetic Communications: An International Journal for Rapid Communication of Synthetic Organic
Chemistry, 37:1, 37-46
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Synthetic Communicationsw, 37: 37–46, 2007
Copyright # Taylor & Francis Group, LLC
ISSN 0039-7911 print/1532-2432 online
DOI: 10.1080/00397910600977574
Facile and Efficient Way to Synthesize the
Radical Cyclization Precursor Methyl
3-(tert-Butyl((E)-3-(2,2-
diphenylcyclopropyl)-2-propenyl)amino)-3-
Oxo-2-(phenylseleno)propanoate for Kinetic
Research
Jindi Yu, Gaoyan Lian, and Danwei Zhang
Department of Chemistry, Fudan University, Shanghai, China
Abstract: Methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-propenyl)amino)-
3-oxo-2-(phenylseleno)propanoate was prepared in 10 steps in good to excellent
yield using benzophenone and hydrazine hydrate as the starting materials.
Keywords: carbene reaction, IBX, phenylselenization, selective reduction, Wittig
reaction
Knowledge of the rate constants of radical reactions is very important because
most useful radical reactions involve chain processes with several competing
pathways available. One can adjust the appropriate reagent concentrations in
advance of experimentation with the knowledge so that the desired sequence
will be efficient. Consequently, research on the rate constants of radical
reactions has received a great deal of attention.[1] Newcomb developed a
general method for direct laser flash photolysis (LFP) measurements of uni-
molecular radical kinetics with ultraviolet (UV) – detectable diphenyl radical
reporter groups [Eq. (1)].[2a] They have used LFP to examine the radical
Received in USA May 5, 2006
Address correspondence to Jindi Yu, Department of Chemistry, Fudan University,
220 Handan Road, Shanghai, China. E-mail: yujindi@msn.com
37

38
J. Yu, G. Lian, and D. Zhang
rearrangement reactions of a number of radicals of phenylselenide derivatives
and pyridinethioneoxycarbonyl (PTOC) ester derivatives.[2]
However, the radicals they examined were limited to all-carbon skeletons.
The radical cyclization percursors containing heteroatoms such as amide ester
have not been studied. Considering that the introduction of a heteroatom will
bring different electronic effects to the whole molecule and further affect the
reaction rate of the radical cyclization, a backbone containing a nitrogen atom
with a diphenyl radical reporter group needs to be synthesized to study the
kinetic character of the radical cyclization. Here we report a facile and
efficient way to a cyclization precursor: methyl 3-(tert-butyl((E)-3-(2,2-diphe-
nylcyclopropyl)-2-propenyl)amino)-3-oxo- 2-(phenylselanyl)propanoate (1).
The coupling of the secondary amine 7 and potassium monomethyl
malonate results in the formation of methyl 3-(tert-butyl((E)-3-(2,2-di-
phenylcyclopropyl)-2-propenyl)amino)-3-oxopropanoate, which could be
converted into the target compound 1 by phenylselenization. The secondary
amine 7 could be generated by the method developed by Frøyen and
Juvvik.[3] The double bond and the three-member ring could be constructed
by modified Wittig reaction and carbene reaction, respectively (Scheme 1).
There are two methods to construct the three-membered ring by the
carbene reaction.
METHOD A
Benzophenone was refluxed with 86% hydrazine hydrate in ethanol to

Radical Cyclization Precursor
39
Scheme 1. Retrosynthetic analysis of the compound 1.
quantitatively yield the corresponding hydrazone. The benzophenone
hydrazone was treated with yellow oxide of mercury,[4] and after filtration,
the purple petroleum ether solution of diphenyldiazomethane was used
directly in the next step. The carbene reaction occurred with the characteristic
phenomenon of decoloration and nitrogen evolution.[5] The yield was good.
METHOD B
1,1-Diphenylethene was quantitatively prepared by Wittig reaction from
benzophenone. Ethyl glycinate hydrochloride was diazotized to ethyl

40
J. Yu, G. Lian, and D. Zhang
diazoacetate.[6] The carbene reaction took place at high temperature, but the
result was not satisfactory.[7]
Comparing these two methods, we found each has its advantage.
Method A’s, advantages are 1) diphenyldiazomethane is relative stable and
safe, 2) the large excess of ethyl acrylate (bp ¼ 998C) can be removed
on a rotary evaporator, 3) the thin-layer chromatography (TLC) is clear.
Its disadvantage is that in the preparation of diphenyldiazomethane, a
by-product is toxic mercury and workup must be careful. Method B’s
advantage is that no toxic substance is produced. Disadvantages are 1)
ethyl diazoacetate is very active and dangerous, and in the preparation, con-
centration of the solvent must be carried out carefully; 2) recovery of the
large excess of 1,1-diphenylethene by column costs great vigor; and 3) the
TLC is messy. Purification is difficult. Method A therefore is superior to
method B.
The synthetic sequence for the generation of compound 1 is depicted in
Scheme 2. In the literature, the alcohol 3 was obtained from ethyl 2,2-diphe-
nylcyclopropanecarboxylate (2) via hydrolysis with potassium hydroxide
followed by reduction of the resulting acid with lithium aluminium
Scheme 2.

Radical Cyclization Precursor
41
hydride (LAH) in dry ether in good yield. However, the yield in the
oxidation was low and the environmentally unfriendly oxidative reagent
pyridinium chlorochromate (PCC) was used.[8]
We directly reduced the ester to alcohol with LiAlH4, skipping the
hydrolysis step. The mild and economic oxidative reagent, IBX(o-iodoxyben-
zoic acid),[9] was used, and the yield was excellent. The construction of
double bond was furnished by a Horner–Wadsworth–Emmons reaction
with triethylphosphonoacetate and sodium hydride in THF in good yield,
and the ester group was selectively reduced by DIBAL-H at 2788C.[10]
The LiAlH4 is not suitable for this situation because it will partly reduce
the double bond. The secondary amine was prepared by a one-pot
synthesis from the alcohol 6 and t-butylamine via alkoxyphosphonium
salt.[3] The coupling of the secondary amine 7 and potassium monomethyl
malonate was carried out employing the couple reagent 1-[3-(dimethylami-
no)propyl]-3-ethylcarbodiimide hydrochloride (EDCI) and N-hydroxybenzo-
triazole (HOBt). EDCI can be neutralized with potassium salt so that the
reaction proceeds smoothly. The amide ester 8 deprotoned by sodium
hydride was treated with phenylselenyl chloride and finally gave the target
compound 1.[11]
In conclusion, we have elaborated a facile and efficient way to the radical
cyclization precursor 1 for kinetic research. Compound 1 was obtained from
commercially available reagents in 10 steps in good to excellent yield. The
related kinetic measurement is in progress.
EXPERIMENTAL
Commercially available reagents were purchased from either the Sinopharm
Group Shanghai Chemical Reagent Company or the Acros chemical
companies and were used as received. Tetrahydrofuran (THF) and diethyl
ether were distilled from sodium benzophenone ketyl. Methylene chloride
1
was distilled from calcium hydride. H NMR spectra (400 MHz) and 13C
NMR spectra (100 MHz) were obtained on EXA 400 spectrometers. Mass
spectra were recorded with a Finnigan MAT 95 mass spectrometer for both
low-resolution and high-resolution mass spectra.

42
J. Yu, G. Lian, and D. Zhang
Ethyl 2,2-Diphenylcyclopropanecarboxylate (2)
Benzophenone hydrazone (2.94 g, 15 mmol), yellow oxide of mercury
(3.25 g, 15 mmol), and 15 ml of petroleum ether were placed in a bottle.
The bottle was wrapped with aluminum foil and stirred slowly at rt for
10 h. The deep purple mixture was filtered to remove mercury and any benzo-
phenone azine. The filtrate was used directly in the next step. A solution of
diphenyldiazomethane in 15 ml of petroleum ether was added in portions,
with stirring, at 508C to ethyl acrylate (2.96 g, 4.3 ml, 39.54 mmol). Each
portion decolorized gradually. The addtion time was about 4 h. The solvent
was removed in vacuo, and the residue was purified by flash column chro-
matography to give 2 (3.23 g, 81%) as a light yellow oil. Analytical TLC
1
(silica gel 60), 20% EtOAc in n-hexane, Rf ¼ 0.74; H NMR (400 MHz,
CDCl3) d 7.36–7.14 (m, 10H), 3.96–3.86 (m, 2H), 2.54 (dd, J ¼ 6.0,
7.8 Hz, 1H), 2.17 (tobs, J ¼ 5.3 Hz, 1H), 1.58 (dd, J ¼ 3.4, 4.8 Hz, 1H),
1.01 (t, J ¼ 7.1 Hz, 3H).
(2,2-Diphenylcyclopropyl)methanol (3)
A solution of 2 (1.646 g, 6.18 mmol) in THF (3 ml) was added dropwise to a
stirred suspension of lithium aluminum hydride (494 mg, 12.36 mmol) in THF
(30 ml). After refluxing for 2.5 h, water was carefully added. The mixture was
transferred into a separatory funnel along with diethyl ether and 30 ml of 5%
HCl soltuion. The layers were separated, and the aqueous layer was extracted
with ether (3 ꢀ 30 ml). The combined organic layer was then dried over
anhydrous Na2SO4. The drier was filtered, and the filtrate was concentrated.
The crude product was purified by flash-column chromatography to give 3
(0.983 g, 71%) as a yellow oil. Analytical TLC (silica gel 60), 20% EtOAc
1
in n-hexane, Rf ¼ 0.41; H NMR (400 MHz, CDCl3) d 7.39–7.12 (m, 10H),
3.50–3.46 (m, 1H), 3.39–3.35 (m, 1H), 2.04–1.98 (m, 1H), 1.40–1.37
(m, 1H), 1.31–1.26 (m, 2H, include -OH).
2,2-Diphenylcyclopropanecarbaldehyde (4)
Compound 3 (0.993 g, 4.43 mmol) was dissolved in EtOAc (30 ml), and
o-iodoxybenzoic acid (IBX) was added. The resulting suspension was
immersed in an oil bath set at 808C and stirred vigorously open to the atmo-
sphere. After 2 h, the reaction mixture was cooled to rt and filtered. The filtrate
was concentrated, and the residue was purified by flash-column chromato-
graphy to give 4 (0.821 g, 83%) as a yellow oil. Analytical TLC (silica gel
60), 20% EtOAc in n-hexane, Rf ¼ 0.80; 1H NMR (400 MHz, CDCl3)
d 8.67 (d, J ¼ 6.9 Hz, 1H), 7.42–7.17 (m, 10H), 2.58–2.52 (m, 1H), 2.26
(dd, J ¼ 5.3, 5.3 Hz, 1H), 1.89 (dd, J ¼ 5.3, 8.5 Hz, 1H).

Radical Cyclization Precursor
43
Ethyl (E)-3-(2,2-diphenylcyclopropyl)acrylate (5)
Ethyl diethylphosphonoacetate (0.937 g, 0.83 ml, 4.18 mmol) was added
dropwise to a suspension of NaH (184 mg, 60% mineral oil dispersion,
4.60 mmol) in THF (4 ml) at 08C over 5 min, and the resulting mixture was
stirring at rt for 30 min. A solution of 4 (0.844 g, 3.8 mmol) in THF (1 ml)
was added to the mixture. The reaction mixture was stirred at reflux for
30 min and then at rt for 12 h. Aqueous NH4Cl solution (1 N) was added to
the mixture. The organic solvent was removed under reduced pressure. The
aqueous layer was extracted by Et2O (3 ꢀ 30 ml). The combined organic
layer was then dried over anhydrous Na2SO4. The drier was filtered, and the
filtrate was concentrated. The crude product was purified by flash-column
chromatography to give 5 (0.907 g, 82%) as a yellow oil. Analytical TLC
1
(silica gel 60), 20% EtOAc in n-hexane, Rf ¼ 0.66; H NMR (400 MHz,
CDCl3) d 7.33–7.14 (m, 10H), 6.24 (dd, J ¼ 10.3, 15.4 Hz, 1H), 5.97
(d, J ¼ 15.1 Hz, 1H), 4.11 (q, J ¼ 7.1 Hz, 2H), 2.39–2.36 (m, 1H), 1.80
(dd, J ¼ 5.0, 8.7 Hz, 1H), 1.71 (tobs, J ¼ 5.3 Hz, 1H), 1.22 (t, J = 7.1 Hz,
3H); 13C NMR (100 MHz, CDCl3) d 166.4, 150.2, 145.6, 140.5, 130.6,
128.7, 128.5, 127.4, 127.2, 126.4, 120.0, 60.1, 39.7, 30.2, 23.4, 14.3; IR
(neat) 2981, 1714, 1643 cm21; LRMS for C20H20O2 (EI, 20 eV) m/z 293
(Mþ þ 1, 5), 292 (Mþ, 31); HRMS (EI) for C20H20O2 (Mþ): calcd.
292.1463, found 292.1467.
(E)-3-(2,2-Diphenylcyclopropyl)prop-2-en-1-ol (6)
Compound 5 (0.665 g, 2.27 mmol) was added to a solution of DIBAL (1 M
solution in toluene, 6.37 ml, 6.37 mmol) and THF (10 ml) at –788C over
5 min, and the resulting mixture was stirred at –788C for 3 h. MeOH (1 ml)
was added to the mixture at –788C, followed by water (1 ml). The mixture
was allowed to warm to rt for 0.5 h. Water (1 ml) was added to the mixture,
followed by 15 wt% aqueous NaOH solution (1 ml). The white precipitate
was filtered, and the filtrate was concentrated in vacuo. The residue was
diluted by Et2O. The aqueous layer was extracted by Et2O (3 ꢀ 30 ml). The
combined organic layer was then dried over anhydrous Na2SO4. The drier
was filtered, and the filtrate was concentrated. The crude product was
purified by flash-column chromatography to give 6 (0.568 g, 100%) as a
yellow oil. Analytical TLC (silica gel 60), 20% EtOAc in n-hexane,
1
Rf ¼ 0.46; H NMR (400 MHz, CDCl3) d 7.39–7.11 (m, 10H), 5.79 (dt,
J ¼ 6.2, 15.6 Hz, 1H), 4.97 (dd, J ¼ 9.4, 15.4 Hz, 1H), 3.96 (d, J ¼ 6.0 Hz,
2H), 2.31–2.25 (m, 1H), 1.59 (dd, J ¼ 5.0, 8.7 Hz, 1H), 1.49 (tobs
,
J ¼ 5.3 Hz, 1H), 1.24 (br, 1H, -OH); 13C NMR (100 MHz, CDCl3) d 146.5,
141.3, 133.9, 130.9, 128.8, 128.4, 127.4, 126.7, 126.0, 63.7, 37.3, 29.6,
22.2; IR (neat) 2925, 1660, 1599 cm21; LRMS for C18H18O (EI, 20 eV) m/z

44
J. Yu, G. Lian, and D. Zhang
250 (Mþ, 9); HRMS (EI) for C18H18O (Mþ): calcd. 250.1358, found
250.1375.
(E)-N-tert-Butyl-3-(2,2-diphenylcyclopropyl)prop-2-en-1-amine (7)
N-Bromosuccimide (404 mg, 2.27 mmol) was added to a stirred solution of
triphenylphosphine (595 mg, 2.27 mmol) and 6 (568 mg, 2.27 mmol) in
anhydrous THF (10 ml) at –208C over 2–3 min in small portions under N2.
After 5 min, tert-butylamine (498 mg, 0.72 ml, 6.81 mmol) was injected via
a syringe in one portion. The temperature was raised to rt naturally
overnight. Petroleum ether (10 ml) was added to the reaction mixture and
stirred for 0.5 h. The phosphine oxide and succinimide solid were precipitated.
The solid was filtered and washed by HCl (1 N). Then the aqueous layer was
neutralized by NaHCO3 solution and extracted by Et2O (3 ꢀ 10 ml). The
combined organic layer was then dried over anhydrous Na2SO4. Filtered
and concentrated. The crude product was purified by flash-column chromato-
graphy to give 7 (632 mg, 91%) as a light yellow oil. Analytical TLC (silica
1
gel 60), 50% EtOAc in n-hexane, Rf ¼ 0.17; H NMR (300 MHz, CDCl3)
d 7.34–7.10 (m, 10H), 5.79 (dt, J ¼ 6.9, 15.1 Hz, 1H), 4.97 (dd, J ¼ 9.2,
15.4 Hz, 1H), 3.03 (ABdd, JAB ¼ 12.1 Hz, J ¼ 0.9, 6.8 Hz, 2H), 2.25 (dt,
J ¼ 5.9, 8.7 Hz, 1H), 1.55 (dd, J ¼ 5.0, 8.7 Hz, 1H), 1.47 (tobs, J ¼ 5.3 Hz,
1H), 1.04 (s, 9H); 13C NMR (100 MHz, CDCl3) d 146.7, 141.5, 132.5,
131.1, 129.3, 128.34, 128.28, 127.4, 126.5, 125.9, 50.4, 45.0, 37.0, 29.7,
29.1, 22.0; IR (neat) 2962, 1599, 1495 cm21; LRMS for C22H27N (EI, 20 eV)
m/z 305 (Mþ, 12); HRMS (EI) for C22H27N (Mþ): calcd. 305.2143, found
305.2172.
Methyl 3-(tert-butyl((E)-3-(2,2-diphenylcyclopropyl)-2-
propenyl)amino)-3-oxopropanoate (8)
Compound 7 (0.632 g, 2.07 mmol), potassium monomethylmalonate (0.388 g,
2.48 mmol), EDCI HCl (0.619 g, 3.23 mmol), and HOBt (0.503 g, 3.73 mmol)
were dissolved in 50 ml CH2Cl2 at 08C and stirred at rt overnight. The white
precipitate was filtered, and the organic layer was washed with saturated
NaHCO3 solution (30 ml) and hydrochloric acid (1 N) (30 ml). It was then
dried over anhydrous Na2SO4. The drier was filtered, and the filtrate was con-
centrated. The crude product was purified by flash-column chromatography to
give 8 (0.631 g, 75%) as a light yellow oil. Analytical TLC (silica gel 60), 50%
1
EtOAc in n-hexane, Rf ¼ 0.43; H NMR (400 MHz, CDCl3) d 7.32–7.12
(m, 10H), 5.55 (dt, J ¼ 4.6, 15.6 Hz, 1H), 4.89 (dd, J ¼ 8.9, 15.3 Hz, 1H),
3.85–3.69 (m, 2H), 3.72 (s, 3H), 3.25 (AB, JAB ¼ 15.1 Hz, 2H), 2.32 (dt,
J ¼ 6.0, 8.7 Hz, 1H), 1.58–1.52 (m, 2H), 1.26 (s, 9H); 13C NMR
(100 MHz, CDCl3) d 168.9, 167.1, 146.3, 141.1, 132.8, 130.8, 128.6, 128.4,

Radical Cyclization Precursor
45
127.4, 126.8, 126.7, 126.1, 57.8, 52.4, 47.1, 43.6, 37.3, 29.4, 28.6, 21.9; IR
(neat) 2958, 1746, 1651 cm21; LRMS for C26H31NO3 (EI, 20 eV) m/z 406
(Mþ þ 1, 19), 405 (Mþ, 42); HRMS (EI) for C26H31NO3 (Mþ): calcd.
405.2304, found 405.2325.
Methyl 3-(tert-butyl((E)3-(2,2-diphenylcyclopropyl)-2-
propenyl)amino)-3-oxo-2-(phenylselanyl)propanoate (1)
A THF (20 ml) solution of 8 (631 mg, 1.56 mmol) was added slowly at 08C to
a stirred suspension of NaH (68 mg, 60% mineral oil dispersion, 1.71 mmol)
in THF (10 ml). After 20 min, phenylselenyl chloride (299 mg, 1.53 mmol)
was added in one portion at 2788C. The reaction was stirred at –788C for
2 h and then quenched with water. After removal of the solvent, the residue
was extracted with Et2O, washed with water, and dried over anhydrous
Na2SO4. After it was filtered and concentrated, the crude product was
purified by precooled column chromatography to give 1 (691 mg, 79%) as a
yellow oil. Analytical TLC (silica gel 60), 50% EtOAc in n-hexane,
1
Rf ¼ 0.56; H NMR (400 MHz, CDCl3) d 7.64–7.12 (m, 15H), 5.52 (dt,
J ¼ 4.1, 15.6 Hz, 0.85 ꢀ 1H), 5.44 (dt, J ¼ 4.6, 15.6 Hz, 0.15 ꢀ 1H), 4.87
(dd, J ¼ 9.4, 15.4 Hz, 1H), 4.63 (s, 0.27 ꢀ 1H), 4.61 (s, 0.77 ꢀ 1H), 3.90–
3.67 (m, 2H), 3.69 (s, 3H), 2.28 (dt, J ¼ 6.0, 8.7 Hz, 1H), 1.53 (dd, J ¼ 5.0,
8.7 Hz, 1H), 1.48 (tobs, J ¼ 5.5 Hz, 1H), 1.22 (s, 9H); 13C NMR (100 MHz,
CDCl3) d 169.7, 166.8, 146.3, 141.1, 135.9, 135.6, 133.0, 130.8, 129.1,
128.8, 128.7, 128.6, 128.4, 127.4, 126.8, 126.1, 58.3, 53.1, 50.4, 47.1, 37.3,
29.5, 28.3, 22.2; IR (neat) 2958, 1732, 1648 cm21
; LRMS for
C32H35NO3Se (EI, 20 eV) m/z 561 (Mþ, 14); HRMS (EI) for C32H35NO3Se
(Mþ): calcd. 561.1782, found 561.1790.
ACKNOWLEDGMENT
Financial support by National Natural Science Foundation of China (Project
No. 20229201) is gratefully acknowledged.
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