I
A. Murre et al.
Paper
Synthesis
trans-1g
IR (KBr): 3010, 2963, 2934, 2838, 1778, 1704, 1605, 1513, 1391, 1296,
1250, 1123, 1035, 883, 755 cm–1
.
1H NMR (400 MHz, CDCl3): = 6.38–6.16 (m, 1 H, CH3CH), 5.71–5.53
(m, 1 H, CHCH2), 5.31 (s, 2 H, COCH2), 4.61–4.55 (m, 2 H, CH2O), 4.52
(d, J = 7.6 Hz, 2 H, CHCH2), 4.17–3.97 (m, 2 H, CH2N), 3.49 (s, 6 H,
N(CH3)2), 1.82 (dd, J = 6.8, 1.4 Hz, 3 H, CH3).
13C NMR (101 MHz, CDCl3): = 164.5, 153.5, 143.0, 117.1, 66.9, 63.6,
63.4, 50.7 (2 C), 42.5, 18.5.
1H NMR (400 MHz, DMSO): = 7.53 (d, J = 8.7 Hz, 2 H, Ar), 6.96 (d,
J = 8.7 Hz, 2 H, Ar), 6.82 (d, J = 15.6 Hz, 1 H, ArCH), 6.33 (dt, J = 15.4,
7.6 Hz, 1 H, CHCH2), 4.79 (s, 2 H, COCH2), 4.46 (t, J = 8.0 Hz, 2 H, CH2O),
4.34 (d, J = 7.5 Hz, 2 H, CHCH2), 3.95 (t, J = 8.0 Hz, 2 H, CH2N), 3.78 (s, 3
H, OCH3), 3.27 (s, 6 H, N(CH3)2).
13C NMR (101 MHz, DMSO): = 164.4, 160.0, 153.3, 141.3, 128.8 (2 C),
127.8, 114.1 (2 C), 113.3, 67.1, 63.5, 61.8, 55.3, 50.7 (2 C), 42.2.
cis-1g
1H NMR (400 MHz, CDCl3): = 6.38–6.16 (m, 1 H, CH3CH), 5.71–5.53
(m, 1 H, CHCH2), 5.42 (s, 2 H, COCH2), 4.62–4.53 (m, 4 H, CHCH2,
CH2O), 4.17–3.97 (m, 2 H, CH2N), 3.52 (s, 6 H, N(CH3)2), 1.92–1.87 (m,
3 H, CH3).
HRMS (ESI): m/z [M]+ calcd for C17H23N2O4: 319.1652; found:
319.1657.
(E)-N,N-Dimethyl-3-(4-nitrophenyl)-N-[2-oxo-2-(2-oxooxazoli-
din-3-yl)ethyl]prop-2-en-1-aminium Bromide (1j)
HRMS (ESI): m/z [M]+ calcd for C11H19N2O3: 227.1390; found:
227.1395.
Following GPB, starting from (E)-N,N-dimethyl-3-(4-nitrophe-
nyl)prop-2-en-1-amine (71 mg, 0.34 mmol) and 3-(2-bromoace-
tyl)oxazolidin-2-one (72 mg, 0.34 mmol). The mixture was stirred for
2 h, then dried under reduced pressure. The obtained solid was
stirred in EtOAc, filtered, and dried under reduced pressure, to afford
the product (100 mg, 70%) as an off-white solid; mp 151–152 °C.
(Z)-N,N-Dimethyl-N-[2-oxo-2-(2-oxooxazolidin-3-yl)ethyl]but-2-
en-1-aminium Bromide (cis-1g)
Following GPB, starting from (Z)-N,N-dimethylbut-2-en-1-amine (59
mg, 0.60 mmol) and 3-(2-bromoacetyl)oxazolidin-2-one (83 mg, 0.40
mmol), the mixture was stirred for 2 h. Drying under reduced pres-
sure gave the crude product (123 mg, quantitative) as a white amor-
phous solid.
IR (KBr): 3061, 3032, 3008, 2923, 1792, 1714, 1599, 1516, 1474, 1343,
1289, 1186, 1107, 1023, 936, 873, 739 cm–1
.
1H NMR (400 MHz, DMSO): = 8.27 (d, J = 8.8 Hz, 2 H, Ar), 7.88 (d,
J = 8.8 Hz, 2 H, Ar), 7.02 (d, J = 15.7 Hz, 1 H, ArCH), 6.78 (dt, J = 15.5,
7.4 Hz, 1 H, CHCH2), 4.85 (s, 2 H, COCH2), 4.55–4.46 (m, 2 H, CH2O),
4.46–4.41 (m, 2 H, CHCH2), 3.96 (t, J = 8.0 Hz, 2 H, CH2N), 3.31 (s, 6 H,
N(CH3)2).
13C NMR (101 MHz, DMSO): = 164.3, 153.2, 147.3, 141.7, 138.8,
128.4 (2 C), 123.9 (2 C), 121.4, 66.1, 63.6, 62.1, 51.1 (2 C), 42.2.
IR (KBr): 3015, 2970, 2922, 1779, 1704, 1477, 1417, 1390, 1298, 1227,
1122, 1038, 882, 755 cm–1
.
1H NMR (400 MHz, CDCl3): = 6.25 (dq, J = 11.1, 7.1 Hz, 1 H, CH3CH),
5.67–5.58 (m, 1 H, CHCH2), 5.43 (s, 2 H, COCH2), 4.64–4.54 (m, 4 H,
CHCH2, CH2O), 4.10 (t, J = 8.0 Hz, 2 H, CH2N), 3.53 (s, 6 H, N(CH3)2),
1.90 (dd, J = 7.1, 1.6 Hz, 3 H, CH3).
13C NMR (101 MHz, CDCl3): = 162.6, 151.5, 138.1, 114.1, 61.7, 61.4,
HRMS (ESI): m/z [M]+ calcd for C16H20N3O5: 334.1397; found:
59.1, 48.8 (2 C), 40.5, 12.3.
334.1405.
HRMS (ESI): m/z [M]+ calcd for C11H19N2O3: 227.1390; found:
227.1392.
(E)-N,N-Dimethyl-3-(naphthalen-2-yl)-N-[2-oxo-2-(2-oxooxazoli-
din-3-yl)ethyl]prop-2-en-1-aminium Bromide (1k)
Following GPB, starting from (E)-N,N-dimethyl-3-(naphthalen-2-
yl)prop-2-en-1-amine (114 mg, 0.54 mmol) and 3-(2-bromoace-
tyl)oxazolidin-2-one (112 mg, 0.54 mmol), the mixture was stirred
for 1.5 h. Recrystallization (MeCN/EtOAc) gave the product (176 mg,
78%) as a white solid; mp 165–166 °C.
N,N-Dimethyl-N-[2-oxo-2-(2-oxooxazolidin-3-yl)ethyl]prop-2-en-
1-aminium Bromide (1h)
Following GPB, starting from N,N-dimethylprop-2-en-1-amine (90
mg, 1.06 mmol) and 3-(2-bromoacetyl)oxazolidin-2-one (200 mg,
0.96 mmol), the mixture was stirred for 2 h. Drying under reduced
pressure gave the crude product (282 mg, quantitative) as a yellow
amorphous solid.
IR (KBr): 3050, 3010, 2954, 2920, 1780, 1704, 1386, 1300, 1219, 1127,
1036, 861, 816, 759, 702 cm–1
.
1H NMR (400 MHz, CDCl3): = 6.17–5.93 (m, 1 H, NCH2CH), 5.84–5.73
(m, 1 H, CHCH2), 5.78–5.71 (m, 1 H, CHCH2), 5.34 (s, 2 H, COCH2),
4.68–4.49 (m, 4 H, CHCH2, CH2O), 4.19–4.00 (m, 2 H, CH2N), 3.54 (s, 6
H, N(CH3)2).
13C NMR (400 MHz, CDCl3): = 162.5, 151.5, 128.4, 122.5, 65.02, 61.8,
61.7, 49.2 (2 C), 40.6.
1H NMR (400 MHz, DMSO): = 8.02 (s, 1 H, Ar), 7.97–7.90 (m, 3 H,
Ar), 7.89–7.83 (m, 1 H, Ar), 7.58–7.50 (m, 2 H, Ar), 7.05 (d, J = 15.6 Hz,
1 H, ArCH), 6.65 (dt, J = 15.3, 7.5 Hz, 1 H, CHCH2), 4.85 (s, 2 H, COCH2),
4.52–4.46 (m, 2 H, CH2O), 4.46–4.41 (m, 2 H, CHCH2), 3.96 (t, J = 8.0
Hz, 2 H, CH2N), 3.32 (s, 6 H, N(CH3)2).
13C NMR (101 MHz, DMSO): = 164.4, 153.3, 141.4, 133.1, 132.9,
132.7, 128.2, 128.1, 127.8, 127.6, 126.7, 126.7, 123.8, 116.7, 66.8, 63.6,
61.9, 50.8 (2 C), 42.2.
HRMS (ESI): m/z [M]+ calcd for C10H17N2O3: 213.1234; found:
213.1237.
HRMS (ESI): m/z [M]+ calcd for C20H23N2O3: 339.1703; found:
339.1714.
(E)-3-(4-Methoxyphenyl)-N,N-dimethyl-N-[2-oxo-2-(2-oxooxazo-
lidin-3-yl)ethyl]prop-2-en-1-aminium Bromide (1i)
(E)-N,N-Dimethyl-N-[2-oxo-2-(2-oxooxazolidin-3-yl)ethyl]-3-
(thiophen-2-yl)prop-2-en-1-aminium Bromide (1l)
Following GPB, starting from (E)-3-(4-methoxyphenyl)-N,N-dimeth-
ylprop-2-en-1-amine (127 mg, 0.66 mmol) and 3-(2-bromoacetyl)ox-
azolidin-2-one (138 mg, 0.66 mmol). The mixture was stirred for 2 h,
then dried under reduced pressure. The obtained solid was stirred in
EtOAc, filtered under argon, and dried under reduced pressure, to af-
ford the product (213 mg, 80%) as an off-white amorphous solid.
Following GPB, starting from (E)-N,N-dimethyl-3-(thiophen-2-
yl)prop-2-en-1-amine (80 mg, 0.48 mmol) and 3-(2-bromoacetyl)ox-
azolidin-2-one (100 mg, 0.48 mmol). The mixture was stirred for 2 h,
© 2019. Thieme. All rights reserved. — Synthesis 2019, 51, A–O