7278
M.C. Sheikh et al. / Tetrahedron 66 (2010) 7272e7278
purified by TLC on silica gel (CH2Cl2) gave the title compound 4h14
by dil AcOH solution and extracted with CH2Cl2. The organic layer
was separated successively washed with water and brine, and dried
over anhydrous MgSO4. Removal of solvent in vacuum gave a solid
product, which was purified by TLC on silica gel (CH2Cl2) gave the
title compound 10 (149.7 mg, 78%) as a colorless solid; mp
(75.2 mg, 95%) as a colorless liquid; 1H NMR (400 MHz, CDCl3)
d
2.87 (t, J¼7.6 Hz, 2H), 3.06 (t, J¼7.6 Hz, 2H), 6.98e7.01 (m, 2H),
7.17e7.33 (m, 8H); 13C NMR (100 MHz, CDCl3)
d
30.9, 35.9, 121.5,
125.7, 126.4, 128.3, 128.5, 129.3, 140.0, 150.6, 171.3; IR (NaCl disc)
1759 cmꢁ1. HRMS (EI) calcd for C22H20O2: 226.0994; found: m/z
226.0990.
99e100 ꢀC (from CH2Cl2/hexane); 1H NMR (400 MHz, CDCl3)
d 0.67
(s, 3H), 0.86 (dd, J¼1.6, 12.8 Hz, 6H), 0.93 (d, J¼6.4 Hz, 3H),
0.94e1.08 (m, 6H), 1.10e1.21 (m, 7H), 1.24e1.40 (m, 4H), 1.42e1.60
(m, 7H), 1.78e1.90 (m, 3H), 1.91e2.02 (m, 2H), 2.27 (d, J¼7.6 Hz,
2H), 2.58e2.62 (m, 2H), 2.94 (t, J¼8.0 Hz, 2H), 4.56e4.65 (m, 1H),
5.36 (d, J¼4.0 Hz, 1H), 7.17e7.21 (m, 3H), 7.25e7.30 (m, 2H); 13C
4.14. Preparation of N-2-phenylethyl-3-phenyl
propanamide 4i
Typical procedure: 2-Phenylethylamine (44.4
m
L, 0.35 mmol)
NMR (100 MHz, CDCl3) d11.8, 18.7, 19.3, 21.0, 22.5, 22.8, 23.8, 24.2,
was added to a stirred solution of 8 (100.0 mg, 0.35 mmol) in
CH2Cl2 (2 mL) at room temperature under N2 and stirred for 8 min.
Then, the reaction mixture was neutralized by dil AcOH solution
and extracted with CH2Cl2. The organic layer was separated, suc-
cessively washed with water and brine, and dried over anhydrous
MgSO4. Removal of solvent in vacuum gave a solid product, which
was purified by TLC on silica gel (AcOEt/hexane¼2:1) gave the title
compound 4i23 (78.9 mg, 89%) as a colorless solid; mp 96e97.5 ꢀC
27.7, 28.0, 28.2, 31.0, 31.8, 31.9, 35.7, 36.1, 36.2, 36.5, 36.9, 38.1, 39.5,
39.7, 42.2, 50.0, 56.1, 56.6, 74.0, 122.6, 126.1, 128.3, 128.4, 139.6,
140.5, 172.3; IR (KBr) 1734 cmꢁ1. Anal. Calcd for C36H54O2: C, 83.34;
H, 10.49. Found: C, 83.39; H, 10.42.
Supplementary data
Supplementary data associated with this article can found in
(from AcOEt/hexane); 1H NMR (400 MHz, CDCl3)
d
2.40 (t, J¼7.6 Hz,
2H), 2.71 (t, J¼7.0 Hz, 2H), 2.92 (t, J¼7.8 Hz, 2H), 3.45 (q, J¼13.4 Hz,
2H), 5.59 (s, 1H), 7.06e7.08 (m, 2H), 7.15e7.28 (m, 8H); 13C NMR
(100 MHz, CDCl3)
d 31.5, 35.5, 38.3, 40.5, 126.1, 126.3, 128.2, 128.4,
References and notes
128.5, 128.6, 138.7, 140.7, 171.9; IR (KBr) 3301, 1637 cmꢁ1. HRMS (EI)
calcd for C17H19NO: 253.1467; found: m/z 253.1466.
1. Takeda, K.; Sawada, I.; Suzuki, A.; Ogura, H. Tetrahedron Lett. 1983, 4451.
2. (a) Chen, S. T.; Wu, S. H.; Wang, K. T. Synthesis 1989, 37; (b) Mahmoud, K. A.;
Long, Yi-T.; Schatte, G.; Kraatz, H.-B. Eur. J. Inorg. Chem. 2005, 173.
3. Nakatsuji, S.; Ikemoto, H.; Akutsu, H.; Yamada, J.; Mori, A. J.Org. Chem. 2003, 68,
1708.
4.15. Preparation of 3-phenyl-2-(3-phenyl-propionylamino)
propionic acid methyl ester 4j
4. (a) Goto, H.; Zhang, H. Q.; Yashima, E. J. Am. Chem. Soc. 2003, 125, 2516; (b)
Michael, C.; Yehuda, K.; Yakir, K. J. Chem. Res. 1977, 8, 202.
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Typical procedure: 4-DMAP (43.0 mg, 0.35 mmol) was added to
a stirred solution of L-phenylalanine methyl ester hydrochloride
(76.2 mg, 0.35 mmol) and 8 (100 mg, 0.35 mmol) in CH2Cl2 at room
temperature under N2 and stirred for 1.5 h. Then, the reaction
mixture was neutralized by dil AcOH solution and extracted with
CH2Cl2. The organic layer was separated, successively washed with
water and brine, and dried over anhydrous MgSO4. Removal of
solvent in vacuum gave a solid product, which was purified by TLC
on silica gel (AcOEt/hexane¼1:1) gave the title compound 4j24
(83.9 mg, 77%) as a colorless solid; mp 70e71.5 ꢀC (from AcOEt/
12. Byung, J. K.; Hiroyuki, M. Chem. Lett. 2000, 1, 42.
hexane); 1H NMR (400 MHz, CDCl3)
d 2.43e2.56 (m, 2H), 2.91e2.96
13. (a) Sheikh, M. C.; Takagi, S.; Sakai, M.; Abe, H.; Morita, H. Org. Biomol. Chem.
2008, 6, 4505; (b) Katrizky, A. R.; Lan, X.; Yang, J. Z.; Denisko, O. V. Chem. Rev.
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14. (a) Takagi, S.; Sheikh, M. C.; Ogasawara, A.; Ohira, M.; Abe, H.; Morita, H.
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Ohira, M.; Miyatake, R.; Abe, H.; Yoshimura, T.; Morita, H. Tetrahedron 2010,
66, 2132.
(m, 2H), 3.06 (d, J¼5.2 Hz, 2H), 3.70 (s, 3H), 4.86e4.91 (m, 1H), 5.83
(d, J¼7.2 Hz, 1H), 6.92e6.94 (m, 2H), 7.18e7.31 (m, 8H); 13C NMR
(100 MHz, CDCl3)
d 31.3, 37.8, 38.1, 52.2, 52.9, 126.2, 127.0, 128.3,
128.5, 129.2, 135.6, 140.6, 171.4, 171.9; IR (KBr) 3324, 1753,
1647 cmꢁ1. HRMS (EI) calcd for C19H21NO3: 311.1521; found: m/z
311.1520.
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4.16. Preparation of 3-phenylpropionyloxycholesterol
ester 10
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Typical procedure: 4-DMAP (41.2 mg, 0.37 mmol) was added to
a stirred solution of cholesterol (144.6 mg, 0.37 mmol) and 6
(100.0 mg, 0.37 mmol) in CH2Cl2 (2 mL) at room temperature under
N2 and stirred for 1 h. Then, the reaction mixture was neutralized