The Journal of Organic Chemistry
Article
7
.35−7.25 (m, 5H), 4.96 (s, 1H), 4.93 (br s, 1H), 4.85 (br s, 1H), 4.77
thank Professors Keith Smith (Cardiff University), Rebecca
Braslau (University of California at Santa Cruz), and Dr.
Christian Goralski (CTG Consulting, LLC Midland, MI, USA)
for helpful discussions.
(
d, 1H, J = 15.2 Hz), 4.28 (t, 1H, J = 7.4 Hz), 4.09−4.01 (m, 2H), 3.39
(
t, 1H, J = 8.8 Hz), 3.19 (d, 1H, J = 17.6 Hz), 2.33 (d, 1H, J = 18.0
13
Hz); C NMR (100 MHz, CD COCD ) δ 172.6, 137.9, 129.3, 129.0,
3
3
1
28.1, 98.2, 82.8, 78.3, 71.4, 43.8, 38.9; IR (KBr) 3373, 1671, 1452
−
1
cm ; HRMS (TOF MS ES+) m/z calcd for C H NaNO (M +
13
15
4
+
Na) 272.0893, found 272.0907.
REFERENCES
,
■
(
S)-Methyl 2-((S)-1-(3,4-Dimethoxyphenethyl)-3-hydroxy-2,5-di-
(
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(
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4
431.
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(
(
(
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0
D
1
3
6
3
2
1
5
.80−6.72 (m, 3H), 4.26 (s, 1H), 3.92 (s, 3H), 3.87 (s, 3H), 3.85 (s,
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5.9, 53.7, 40.2, 39.6, 32.8; IR (ATR) 3466, 2952, 1790, 1739, 1700
3
−1
+
cm ; HRMS (TOF MS ES+): m/z calcd for C H NO (M + H)
17
22
8
3
68.1340, found 368.1333.
1R,10bR)-1-((R)-1,2-Dihydroxyethyl)-1-hydroxy-8,9-dimethoxy-
,5,6,10b-tetrahydropyrrolo[2,1-a]isoquinolin-3(2H)-one (44). A dry
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(
1
(
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equipped with a magnetic stir bar and fitted with a rubber septum
was charged with pyrrolidinedione (43) (0.92g, 2.5 mmol), methanol
(
2
(
(
5 mL), and 5 mol % of NaOMe (0.125 mmol) at 25 °C. Powdered
NaBH (283.7 mg, 7.5 mmol) was added in one portion to the
4
(13) Narasimhan, S.; Madhavan, S.; Prasad, K. G. J. Org. Chem. 1995,
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6
0, 5314.
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(
Caution! Hydrogen evolution) and concentrated under vacuum
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1
(
991, 64, 2730.
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CHCl /MeOH (1−3% MeOH) mixture as eluent to afford 44 as a
3
2
0
white solid (0.616 mg, 0.19 mmol) in 70% yield: [α] −156.6 (c =
D
1
0
7
.11. methanol); mp 99−102 °C; H NMR (CD OD, 400 MHz) δ
3
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2
1
5
.74−3.69 (m, 1H), 2.92−2.79 (m, 3H), 2.63 (d, J = 14.8 Hz, 1H),
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3
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−1
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MS ES+) m/z calcd for C H NO Na (M + Na) 346.1261, found
16
21
6
(
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346.1256.
4
(
ASSOCIATED CONTENT
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*
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M.; Mendonca, J. S.; de Souza, M. V. N.; Peralta, M. A.; Vasconcelos,
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(
(
AUTHOR INFORMATION
■
(
*
*
(
ORCID
(
Notes
The authors declare no competing financial interest.
(
(
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ACKNOWLEDGMENTS
■
8421.
We acknowledge DST (Government of India) for financial
support via DST Project No. SR/S1/OC-98/2012 (SERB). We
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M.; Baxendale, I. R. Org. Lett. 2012, 14, 696.
I
J. Org. Chem. XXXX, XXX, XXX−XXX