Notes
J . Org. Chem., Vol. 64, No. 15, 1999 5727
SEMCl (c) according to the general procedure. Pure 1c
was obtained as a yellow oil by flash chromatography
(hexane/AcOEt ) 4:1) in 48% yield: 1H NMR (CDCl3, 400
MHz) δ 7.29-7.25 (m, 2H), 7.08-7.03 (m, 2H), 5.15 (s,
2H), 3.61-3.57 (m, 4H), 0.95-0.90 (m, 2H), 0.02-0.04
(m, 9H); 13C NMR (CDCl3, 100 MHz) δ 175.4 (s), 143.7
(s), 127.9 (d), 124.3 (d), 124.0 (s), 122.7 (d), 109.6 (d), 69.4
(t), 66.1 (t), 35.9 (t), 17.8 (t), 1.5 (q); LRMS (EI, m/z) 263
(M+); HRMS (EI, m/z) for C14H21NO2Si calcd 263.1342,
found 263.1348.
N-Ben zyloxym eth yloxin d ole (1d ). Compound 1d
was prepared by the reaction of 1 with BOMCl (d )
according to the general procedure. Pure 1d was obtained
as a white solid by flash chromatography (hexane/AcOEt
) 3:1) in 55% yield: mp 74-76 °C; 1H NMR (CDCl3, 400
MHz) δ 7.30-7.23 (m, 7H), 7.07-7.05 (m, 2H), 5.26 (s,
2H), 4.57 (s, 2H), 3.54 (s, 2H); 13C NMR (CDCl3, 100 MHz)
δ 175.5 (s), 143.4 (s), 137.3 (s), 128.5 (s), 128.3 (d), 128.0
(s), 127.8 (s), 124.4 (d), 124.0 (s), 122.8 (d), 109.6 (d), 70.8
(t), 69.6 (t), 35.8 (t); LRMS (EI, m/z) 253 (M+); HRMS
(EI, m/z) for C16H15NO2 calcd 253.1104, found 253.1108.
Anal. Calcd for C16H15NO2: C, 75.87; H, 5.97; N, 5.53.
Found: C, 75.59; H, 6.07; N, 5.46.
N -Met h oxym et h yl-3,4-d ih yd r o -2-(1H)-q u in olin -
on e (2a ). Compound 2a was prepared by the reaction of
2 with MOMCl (a ) according to the general procedure.
Pure 2a was obtained as a white solid by flash chroma-
tography (hexane/AcOEt ) 2:1) in 98% yield: mp 55-57
°C; 1H NMR (CDCl3, 400 MHz) δ 7.31-7.00 (m, 4H), 5.31
(s, 2H), 3.40 (s, 3H), 2.93-2.89 (m, 2H), 2.71-2.67 (m,
2H); 13C NMR (CDCl3, 100 MHz) δ 171.1 (s), 139.4 (s),
127.5 (d), 127.5 (d), 125.9 (s), 123.3 (d), 115.8 (d), 73.8
(t), 56.1 (q), 31.7 (t), 25.2 (t); LRMS (EI, m/z) 191 (M+);
HRMS (EI, m/z) for C11H13NO2 calcd 191.0947, found
191.0944. Anal. Calcd for C11H13NO2: C, 69.09; H, 6.85;
N, 7.32. Found: C, 68.94; H, 6.95; N, 7.24.
(t), 71.5 (t), 66.0 (t), 31.9 (t), 25.4 (t), 18.1 (t), 1.4 (t); LRMS
(EI, m/z) 277 (M+); HRMS (EI, m/z) for C15H23NO2Si calcd
277.1499, found 277.1496.
N-Ben zyloxym et h yl-3,4-d ih yd r o-2-(1H )-q u in oli-
n on e (2d ). Compound 2d was prepared by the reaction
of 2 with BOMCl (d ) according to the general procedure.
Pure 2d was obtained as a colorless oil by flash chroma-
tography (hexane/AcOEt ) 5:1) in 99% yield: 1H NMR
(CDCl3, 400 MHz) δ 7.40-7.01 (m, 9H), 5.45 (s, 2H), 4.65
(s, 2H), 2.89-2.85 (m, 2H), 2.67-2.63 (m, 2H); 13C NMR
(CDCl3, 100 MHz) δ 171.3 (s), 139.6 (s), 137.9 (s), 128.2
(d), 127.7 (d), 127.6 (d), 126.0 (s), 123.4 (d), 116.1 (d), 72.6
(t), 71.0 (t), 31.8 (t), 25.3 (t); LRMS (EI, m/z) 267 (M+);
HRMS (EI, m/z) for C17H17NO2 calcd 267.1260, found
267.1266.
Gen er a l P r oced u r e for Hyd r id e Red u ction of
Eth er -P r otected Oxin d ole (1a -d ) a n d 3,4-Dih yd r o-
2-(1H)-qu in olin on e (2a -d ). To a solution of ether-
protected aromatic lactam 1a -d or 2a -d (0.3 mmol) in
dry EtOH (6 mL) was added sodium borohydride (4.5
mmol) in one protion at 0 °C, and then the mixture was
stirred at room temperature for 24-48 h. The reaction
was diluted with CH2Cl2 and washed twice with water.
The combined aqueous phases were extracted three times
with CH2Cl2. The combined organic phases were dried
over MgSO4 and concentrated under vacumn. The crude
product was subjected to flash chromatography (CH2Cl2/
MeOH ) 30:1) to give the corresponding compounds 3
or 4. The reaction yields are shown in Table 1.
2-(2-Meth yla m in op h en yl)eth a n ol (3): yellow oil; 1H
NMR (CDCl3, 400 MHz) δ 7.16 (td, J ) 7.8, 1.6 Hz, 1H),
7.01 (dd, J ) 7.5, 1.6 Hz, 1H), 6.70 (td, J ) 7.5, 1.4 Hz,
1H), 6.64 (dd, J ) 8.0, 1.2 Hz, 1H), 3.79 (t, J ) 6.3 Hz,
2H), 3.14 (br s, -NH and -OH, 2H), 2.81 (s, 3H), 2.71
(t, J ) 6.3 Hz); 13C NMR (CDCl3, 400 MHz) δ 147.6 (s),
130.0 (d), 127.8 (d), 123.7 (s), 117.3 (d), 110.3 (d), 62.8
(t), 34.6 (t), 30.7 (q); IR (neat) 3400, 2839, 1613, 1521
cm-1; LRMS (EI, m/z) 151 (M+); HRMS (EI, m/z) for
C9H13NO calcd 151.0998, found 151.0993.
N-(2-Met h oxyet h oxym et h yl)-3,4-d ih yd r o-2-(1H )-
qu in olin on e (2b). Compound 2b was prepared by the
reaction of 2 with MEMCl (b) according to the general
procedure. Pure 2b was obtained as a colorless oil by
flash chromatography (hexane/AcOEt ) 2:1) in 90%
yield: 1H NMR (CDCl3, 400 MHz) δ 7.39 (d, J ) 8.1 Hz,
1H), 7.24-7.03 (m, 3H), 5.41 (s, 2H), 3.76-3.74 (m, 2H),
3.55∼3.53 (m, 2H), 3.37 (s, 3H), 2.93-2.89 (m, 2H), 2.71-
2.67 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 171.2 (s),
139.6 (s), 127.5 (d), 127.4 (d), 125.8 (s), 123.3 (d), 116.1
(d), 72.9 (t), 71.5 (t), 67.8 (t), 58.8 (q), 31.7 (t), 25.2 (t);
3-(2-Meth yla m in op h en yl)p r op a n -1-ol (4): yellow
1
oil; H NMR (CDCl3, 400 MHz) δ 7.16 (td, J ) 7.9, 1.3
Hz, 1H), 7.05 (dd, J ) 7.3, 1.3 Hz, 1H), 6.71 (td, J ) 7.3,
1.1 Hz, 1H), 6.65 (dd, J ) 7.9, 1.0 Hz, 1H), 3.67 (t, J )
5.9 Hz, 2H), 2.87 (s, 3H), 2.60 (t, J ) 7.4 Hz), 1.90-1.83
(m, 2H); 13C NMR (CDCl3, 400 MHz) δ 147.0 (s), 129.1
(d), 127.3 (d), 125.5 (s), 117.3 (d), 110.1 (d), 61.9 (t), 31.8
(t), 30.9 (q), 26.9 (t); IR (CCl4) 3418, 2930, 1613, 1507
cm-1; LRMS (EI, m/z) 165 (M+); HRMS (EI, m/z) for
C10H15NO calcd 165.1155, found 165.1153.
LRMS (EI, m/z) 235 (M+); HRMS (EI, m/z) for C13H17
-
NO3 calcd 235.1209, found 235.1202.
N-[2-(Tr im eth ylsilyl)eth oxym eth yl]-3,4-d ih yd r o-
2-(1H)-qu in olin on e (2c). Compound 2c was prepared
by the reaction of 2 with SEMCl (c) according to the
general procedure. Pure 2c was obtained as a colorless
oil by flash chromatography (hexane/AcOEt ) 5:1) in 99%
yield: 1H NMR (CDCl3, 400 MHz) δ 7.36 (dd, J ) 8.1,
0.7 Hz, 1H), 7.27-7.23 (m, 1H), 7.16-7.15 (m, 1H), 7.04
(td, J ) 7.3, 1.1 Hz, 1H), 5.35 (s, 2H), 3.69-3.65 (m, 2H),
2.94-2.90 (m, 2H), 2.71-2.67 (m, 2H), 0.98-0.94 (m, 2H),
0 (s, 9H); 13C NMR (CDCl3, 100 MHz) δ 171.1 (s), 139.7
(s), 127.5 (d), 127.5 (d), 126.0 (s), 123.3 (d), 116.2 (d), 72.2
Ack n ow led gm en t. We would like to thank the
National Science Council of the Republic of China for
financial support. We thank Ms. Chyi-J iai Wang for
technical assistance.
Su p p or tin g In for m a tion Ava ila ble: Spectral data (Vari-
an Unity Plus 400 MHz 1H NMR and 100 MHz 13C DEPT
NMR) for compounds 1a -d , 2a -d , 3, and 4. This material is
J O990549K