6
Tetrahedron
N- MANRi
4
.11. (3R,5S,E)-methyl 7-(4-(4-fluorophenyl)
A
-6-
C
iso
C
pr
E
op
P
y
T
l-2
E
-(
D
U
ch
S
ha
C
riy
R
a,IPS.
T
; Divya, P.; Meeran, H. N.; Tewari, N. WO
methylmethylsulfonamido)pyrimidin-5-yl)-3,5-dihydroxyhept-6-
Patent 2011132172, 2011; Chem. Abstr. 2011, 155, 589162.
enoate (16).
4
. (a) Satomi, T.; Keiichi, Y.; Noboru, U. Eur. Patent 0374922,
1989; Chem. Abstr. 1991, 114, 61543; (b) Günther, W.; Kurt,
K.; Ekkehard, B.; Gerhard, B. Eur. Patent 0319847, 1990;
Chem. Abstr. 1990, 112, 55602; (c) Wess, G.; Kesseler, K.;
Baader, E.; Bartmann, W.; Beck, G.; Bergmann, A.; Jendralla,
H.; Bock, K.; Holzstein, G.; Kleine, H.; Schnierer, M.
Tetrahedron Lett. 1990, 31, 2545–2548; (d) Hayashi, S.; Inoue,
K.; Koga, T. Eur. Patent 464817, 1992; Chem. Abstr. 1992,
116, 193719; (e) Kizaki, N.; Yasohara, Y.; Yasohara, Y.;
Miyazaki, M.; Mitsuda, M.; Kondo, T.; Ueyama, N.; Inoue, K.
WO Patent 0008011, 2000; Chem. Abstr. 2000, 132, 166230;
(f) Reddy, P. P.; Yen, K. F.; Uang, B. J. J. Org. Chem. 2002,
67, 1034–1035; (g) Lee, I.; Lee, S. WO Patent 2003053950,
2003; Chem. Abstr. 2003, 139, 85359; (h) Shin, H. I.; Choi, B.
S.; Lee, K. K.; Choi, H.; Chang, J. H.; Lee, K. W.; Nam, D. H.;
Kim, N. S. Synthesis 2004, 16, 2629–2632; (i) Choi, H.; Shin,
H. Synlett 2008, 1523–1525; (j) Sun, L.; Zhang, F. Q.; Du, T.
J.; Fang, L. P.; Meng, F. M.; Liu, L. CN Patent 102180862,
2011; Chem. Abstr. 2011, 155, 457681; (k) Tararov, V. I.;
König, G.; Börner, A. Adv. Synth. Catal. 2006, 348, 2633–
To a stirred solution of 15 (268 mg, 0.5 mmol) in 5 mL
acetonitrile at 40 C was added hydrochloric acid (1.25 mL, 0.02
o
M, 0.025 mmol) dropwise. The reaction mixture was stirred at 40
o
C for 8 h before being quenched by Et N and removed solvent
3
under reduced pressure. The residue was purified by column
chromatography (silica gel, EtOAc/PE, 1:1) to afford 16 (205
1
6
1
3.5
mg, 83%) as a colorless spumy solid; [α]
-4.7 (c 1.0, CHCl3);
D
1
H NMR (400 MHz, CDCl ) δ 1.26 (d, J = 6.8 Hz, 6H), 1.35-1.60
3
(m, 2H), 2.43-2.51 (m, 2H), 3.36 (hept, J = 6.8 Hz,1H), 3.51 (s,
3
H), 3.56 (s, 3H), 3.72 (s, 3H), 4.21 (m, 1H), 4.45 (m, 1H), 5.46
(dd, J = 5.2, 16.0 Hz, 1 H), 6.63 (d, J = 16.0 Hz, 1H), 7.08 (t, J =
1
3
8
.4 Hz, 2H), 7.63 (dd, J = 6.0, 8.0 Hz, 2H); C NMR (100 MHz,
CDCl ) δ 21.6, 21.6, 32.1, 33.1, 41.1, 41.8, 42.4, 51.9, 68.4, 71.9,
3
1
1
1
15.0 (d, JC-F = 21.5 Hz), 121.4, 122.7, 132.1 (d, JC-F = 8.3 Hz),
34.5 (d, JC-F = 3.2 Hz), 139.3, 157.2, 163.2 (d, JC-F+= 248.2 Hz),
63.5, 172.9, 174.9; MS (ESI): m/z = 496 (M + H ), 518 (M +
+
Na ); IR (KBr): 3462, 2966, 2931, 2871, 1732, 1548, 1438, 1386,
-
1
1
152, 964, 840, 795 cm .
4
.12. Rosuvastatin calcium (1).
2
644; (l) Bonini, C.; Campaniello, M.; Chiummiento, L.;
To a stirred solution of 16 (149 mg, 0.3 mmol) in MeOH (2
Videtta, V. Tetrahedron 2008, 64, 8766–8772.
o
mL) at 0 C was added NaOH (0.36 mL, 1.0 M, 0.36 mmol), then
o
5. (a) Böger, H. G. A.; Kebeler, K. A. Ger. Patent 4128345, 1991;
Chem. Abstr. 1993, 119, 250383; (b) Urabe, H.; Matsuka, T.;
Sate, F. Tetrahedron Lett. 1992, 33, 4183–4186; (c) Beck, G.;
Jendralla, H.; Kesseler, K. Synthesis 1995, 8, 1014–1018; (d)
Urabe, H.; Matsuka, T. Jpn. Patent 2005082591, 2005; Chem.
Abstr. 2005, 142, 336369; (e) Fan, W.; Li, W.; Ma, X.; Tao, X.;
Li, X.; Yao, Y.; Xie, X.; Zhang, Z. J. Org. Chem. 2011, 76,
reacted at 0 C for 1 h before being added the solution of CaCl
2
o
(
0
1.5 mL, 0.2 M, 0.3 mmol). The mixture was stirred at 20 C for
.5 h before filtrated the resulting white slurry, washed and dried
in vacuum to afford 1 (133 mg, 89%) as a white powder; mp 145-
o
17
o
14.5
D
1
1
49 C, Lit. : mp 145-150 C; [α]
-7.3 (c 0.5, CHCl ); H
3
NMR (400 MHz, CDCl ) δ 1.20 (d, J = 6.0 Hz, 6H), 1.28-1.36
3
(
1
4
m, 1H), 1.47-1.54 (m, 1H), 1.97-2.03 (m, 1H), 2.12-2.16 (m,
H), 3.36-3.43 (m, 1H), 3.43 (s, 3H) 3.54 (s, 3H), 3.76 (m, 1H),
.20 (m, 1H), 5.52 (dd, J = 5.6, 16.0 Hz, 1H), 6.50 (d, J = 16.0
9
444–9451.
6. (a) Takahashi, K.; Minami, T.; Hiyama, T. Tetrahedron Lett.
1993, 34, 513–516; (b) Hiyama, T.; Minami, T.; Takahashi, K.
Bull. Chem. Soc. Jpn. 1995, 68, 364–372; (c) Solladié, G.;
Bauder, C.; Rossi, L. J. Org. Chem. 1995, 60, 7774–7777; (d)
Honda, T.; Ono, S.; Mizutani, H.; Hallinan, K. O. Tetrahedron:
Asymmetry 1997, 8, 181–184; (e) Reddy, M. V. R.; Brown, H.
C.; Ramachandran, P. V. J. Organomet. Chem. 2001, 624,
239–243.
Hz, 1H), 7.27 (t, J = 8.4 Hz, 2H), 7.70 (dd, J = 6.0, 8.0 Hz, 2H);
+
+
MS (ESI): m/z = 482 (acid, M + H ), 504 (acid, M + Na ); IR
(
8
KBr): 3376, 2973, 2931, 2875, 1604, 1548, 1442, 1073, 968,
-
1
44, 776 cm .
Supplementary data
1
13
Copies of H, C NMR, HPLC and GC-MS spectra for the
compounds. Supplementary data related to this article can be
found at ……
7
. (a) Gijsen, H. J. M.; Wong, C. H. J. Am. Chem. Soc. 1994, 116,
422–8423; (b) Scialdone, M. A.; Johnson, C. R. Tetrahedron
8
References and Notes
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