Job/Unit: O43511
/KAP1
Date: 04-02-15 14:28:16
Pages: 10
E. J. Kang et al.
FULL PAPER
δ = 7.70 (d, J = 8.2 Hz, 2 H), 7.32 (d, J = 7.9 Hz, 2 H), 7.29–7.16
(m, 3 H), 7.05 (d, J = 6.8 Hz, 2 H), 3.42–3.31 (m, 2 H), 3.19 (dt, J
3-Benzyl-4-methyl-1-tosylpyrrolidine (2i): Yield 52.1 mg (79%);
white solid; Rf = 0.47 (hexane/EtOAc, 4:1). 1H NMR(300 MHz,
= 9.2, 8.0 Hz, 1 H), 2.91 (dd, J = 9.9, 7.5 Hz, 1 H), 2.54 (d, J = CDCl3): δ = 7.69 (d, J = 8.2 Hz, 2 H), 7.32 (d, J = 7.9 Hz, 2 H),
7.7 Hz, 2 H), 2.44 (s, 3 H), 2.37–2.27 (m, 1 H), 1.90–1.84 (m, 1 H), 7.29–7.16 (m, 3 H), 7.03 (d, J = 6.8 Hz, 2 H), 3.39 and 3.09 (ABX,
1.55–1.46 (m, 1 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 143.3, JAB = 9.7, JAX = 6.4, JBX = 4.2 Hz, 2 H), 3.24 and 3.01 (ABX, JAB
139.7, 133.6, 129.6, 128.5, 128.4, 127.4, 126.2, 52.7, 47.4, 40.3, 39.0,
31.0, 21.5 ppm. HRMS (EI): m/z calcd. for C18H21NO2S [M+]
315.1293; found 315.1299.
= 9.8, JAX = 6.5, JBX = 7.0 Hz, 2 H), 2.64 (d, J = 7.5 Hz, 1 H),
2.44 (s, 3 H), 2.37–2.29 (m, 2 H), 2.25–2.19 (m, 1 H), 0.85 (d, J =
7.0 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 143.3, 139.8,
134.1, 129.6, 128.6, 127.4, 126.3, 54.6, 50.8, 43.6, 35.3, 33.8, 21.6,
13.3 ppm. HRMS (EI): m/z calcd. for C19H23NO2S [M+] 329.1449;
found 329.1445.
3-(4-Chlorobenzyl)-1-tosylpyrrolidine (2d): Yield 48.3 mg (69%);
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white solid; Rf = 0.36 (hexane/EtOAc, 4:1). H NMR (300 MHz,
CDCl3): δ = 7.69 (d, J = 8.0 Hz, 1 H), 7.32 (d, J = 8.1 Hz, 2 H),
7.23 (d, J = 8.0 Hz, 2 H), 6.98 (d, J = 8.1 Hz, 2 H), 3.42–3.28 (m,
2 H), 3.18 (q, J = 8.4 Hz, 1 H), 2.89 (dd, J = 9.7, 7.5 Hz, 1 H),
2.52 (d, J = 7.3 Hz, 2 H), 2.44 (s, 3 H), 2.34–2.23 (m, 1 H), 1.89–
1.84 (m, 1 H), 1.53–1.44 (m, 1 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 143.4, 138.1, 133.8, 132.1, 129.9, 129.6, 128.6, 127.5,
52.6, 47.3, 40.3, 38.4, 31.0, 21.6 ppm. HRMS (EI): m/z calcd. for
C18H20ClNO2S [M+] 422.2603; found 422.2600.
3-Benzyltetrahydrofuran (2j):[30] Yield 3.6 mg (11%); colorless oil;
Rf = 0.42 (hexane/EtOAc, 4:1). H NMR(300 MHz, CDCl3): δ =
1
7.32–7.27 (m, 2 H), 7.23–7.17 (m, 3 H), 3.94–3.72 (m, 3 H), 3.47
(dd, J = 8.4, 6.6 Hz, 1 H), 2.70 (d, J = 8.4 Hz, 2 H), 2.56–2.49 (m,
1 H), 2.06–1.96 (m, 1 H), 1.68–1.60 (m, 1 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 140.8, 128.7, 128.4, 126.1, 73.0, 67.9, 41.0,
39.3, 32.1 ppm. HRMS (EI): m/z calcd. for C11H14O [M+]
162.1045; found 162.1049.
3-(Naphthalen-1-ylmethyl)-1-tosylpyrrolidine (2e): Yield 59.9 mg
(82%); white solid; Rf = 0.38 (hexane/EtOAc, 4:1). 1H NMR
(300 MHz, CDCl3): δ = 7.81–7.76 (m, 2 H), 7.65 (d, J = 8.2 Hz, 1
H), 7.61 (d, J = 8.2 Hz, 2 H), 7.42–7.38 (m, 2 H), 7.29 (t, J =
7.6 Hz, 1 H), 7.21 (d, J = 8.0 Hz, 1 H), 7.10 (d, J = 7.0 Hz, 1 H),
3.40–3.33 (m, 1 H), 3.24 (dd, J = 9.8, 7.2 Hz, 1 H), 3.15–3.07 (m,
1 H), 2.99–2.93 (m, 1 H), 2.92 (d, J = 7.7 Hz, 2 H), 2.49–2.40 (m,
1 H), 2.34 (s, 3 H), 1.82–1.74 (m, 1 H), 1.55–1.48 (m, 1 H) ppm.
13C NMR (75 MHz, CDCl3): δ = 143.3, 135.7, 133.8, 131.6, 129.6,
128.9, 127.5, 127.2, 126.5, 125.9, 125.6, 125.4, 123.4, 53.0, 47.3,
39.2, 36.1, 31.3, 21.5 ppm. HRMS (EI): m/z calcd. for C22H23NO2S
[M+] 365.1449; found 365.1447.
4-Benzyl-2-ethoxytetrahydrofuran (2k):[31] Yield 19.0 mg (46%); col-
orless oil; Rf = 0.78 (hexane/EtOAc, 4:1). 1H NMR (300 MHz,
CDCl3): δ = 7.30–7.28 (m, 2 H), 7.21–7.15 (m, 3 H), 5.14–5.11 (m,
1 H), 3.90 (t, J = 7.8 Hz, 1 H), 3.76 (dq, J = 9.6, 7.1 Hz, 1 H), 3.61
(t, J = 8.5 Hz, 1 H), 3.45 (dq, J = 9.6, 7.1 Hz, 1 H), 2.78 (d, J =
8.3 Hz, 1 H), 2.53–2.43 (m, 1 H), 2.25–2.15 (m, 1 H), 1.66–1.58 (m,
1 H), 1.23 (t, J = 7.1 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl3):
δ = 140.8, 128.6, 128.4, 126.0, 104.4, 71.6, 63.1, 40.1, 39.1, 38.7,
15.3 ppm.
3-Benzyl-5-ethoxy-2,2-dimethyltetrahydrofuran (2l): Yield 27.2 mg
(58%); white solid; Rf = 0.70 (hexane/EtOAc, 4:1). 1H NMR
(300 MHz, CDCl3): δ = 7.30–7.24 (m, 2 H), 7.21–7.16 (m, 3 H),
5.04–4.98 (m, 1 H), 3.80–3.68 (m, 1 H), 3.44–3.34 (m, 1 H), 2.73–
2.68 (m, 1 H), 2.57–2.44 (m, 2 H), 1.78–1.73 (m, 1 H), 1.30–1.13
(m, 9 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 140.7, 128.7,
128.6, 128.4, 128.3, 126.0, 102.8, 83.4, 62.1, 47.6, 39.0, 36.4, 29.7,
23.8, 15.3 ppm. HRMS (EI): m/z calcd. for C15H22O2 [M+]
234.1620; found 234.1621.
3-(Thiophen-2-ylmethyl)-1-tosylpyrrolidine (2f): Yield 48.9 mg
(76%); white solid; Rf = 0.37 (hexane/EtOAc, 4:1). 1H NMR
(300 MHz, CDCl3): δ = 7.70 (d, J = 8.0 Hz, 2 H), 7.32 (d, J =
7.9 Hz, 2 H), 7.12 (d, J = 5.0 Hz, 1 H), 6.91–6.88 (m, 1 H), 6.71
(br. s, 1 H), 3.42–3.34 (m, 2 H), 3.25–3.16 (m, 1 H), 2.95 (dd, J =
9.8, 7.2 Hz, 1 H), 2.75 (d, J = 7.5 Hz, 2 H), 2.44 (s, 3 H), 2.43–2.31
(m, 1 H), 1.98–1.91 (m, 1 H), 1.59–1.49 (m, 1 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 143.4, 142.1, 129.6, 127.5, 126.8, 125.1,
123.7, 52.7, 47.3, 40.6, 33.2, 31.0, 21.5 ppm. HRMS (EI): m/z calcd.
for C16H19NO2S2 [M+] 321.0857; found 321.0865.
5-Ethoxy-2,2-dimethyl-3-(4-methoxybenzyl)tetrahydrofuran
(2m):
Yield 30.7 mg (58%); white solid; Rf = 0.59 (hexane/EtOAc, 4:1).
1H NMR (300 MHz, CDCl3): δ = 7.09 (dd, J = 14.6, 4.3 Hz, 2 H),
6.82 (dd, J = 14.2, 3.2 Hz, 2 H), 5.04–4.97 (m, 1 H), 3.79 (s, 3 H),
3.74–3.69 (m, 1 H), 3.44–3.34 (m, 1 H), 2.51–2.40 (m, 2 H), 1.80–
1.67 (m, 1 H), 1.29–1.12 (m, 9 H) ppm. 13C NMR (75 MHz,
CDCl3): δ = 157.8, 132.8, 129.6, 129.5, 113.73, 113.70, 101.6, 82.7,
62.1, 55.3, 50.5, 47.7, 39.0, 29.7, 23.2, 15.3 ppm. HRMS (EI): m/z
calcd. for C16H24O2S [M+] 248.1776; found 248.1771.
3-Benzyl-1-phenylpyrrolidine (2g): Yield 34.7 mg (73%); white solid;
1
Rf = 0.76 (hexane/EtOAc, 4:1). H NMR(300 MHz, CDCl3): δ =
7.34–7.28 (m, 2 H), 7.25–7.18 (m, 5 H), 6.65 (t, J = 7.2 Hz, 1 H),
6.53 (d, J = 8.0 Hz, 2 H), 3.43–3.37 (m, 1 H), 3.34–3.24 (m, 1 H),
3.02 (t, J = 8.2 Hz, 1 H), 2.76 (d, J = 7.5 Hz, 2 H), 2.64–2.54 (m,
1 H), 2.14–2.04 (m, 1 H), 1.80–1.68 (m, 1 H) ppm. 13C NMR
(75 MHz, CDCl3): δ = 147.8, 140.7, 129.1, 128.7, 128.4, 126.1,
115.3, 111.4, 53.0, 47.2, 40.5, 39.9, 31.4 ppm. HRMS (EI): m/z
calcd. for C17H16N [M+] 237.1517; found 237.1522.
5-Ethoxy-2,2-dimethyl-3-(naphthalen-1-ylmethyl)tetrahydrofuran
(2n): Yield 36.4 mg (64%); white solid; Rf = 0.62 (hexane/EtOAc,
1
4:1). H NMR (300 MHz, CDCl3): δ = 7.99 (d, J = 7.7 Hz, 1 H),
7.85 (d, J = 7.3 Hz, 1 H), 7.72 (d, J = 8.2 Hz, 1 H), 7.54–7.45 (m,
2 H), 7.40–7.29 (m, 2 H), 5.00–4.96 (m, 1 H), 3.71–3.65 (m, 1 H),
3.41–3.28 (m, 2 H), 2.79–2.71 (m, 1 H), 2.63–2.57 (m, 1 H), 2.10–
2.00 (m, 1 H), 1.88–1.78 (m, 1 H), 1.45 (s, 3 H), 1.26 (s, 3 H), 1.09
(t, J = 7.0 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl3): δ = 136.7,
133.9, 128.8, 126.9, 126.5, 125.8, 125.5, 125.4, 125.3, 123.4, 101.6,
83.5, 62.1, 46.4, 39.2, 33.3, 29.6, 23.8, 15.2 ppm. HRMS (EI): m/z
calcd. for C19H24O2 [M+] 284.1776; found 284.1775.
3-(4-Methoxybenzyl)-4-methyl-1-tosylpyrrolidine
(2h):
Yield
48.9 mg (68%); white solid; Rf = 0.43 (hexane/EtOAc, 4:1). 1H
NMR(300 MHz, CDCl3): δ = 7.69 (d, J = 8.4 Hz, 2 H), 7.31 (d, J
= 8.1 Hz, 2 H), 6.95 (d, J = 8.4 Hz, 2 H), 6.79 (d, J = 8.4 Hz, 2
H), 3.78 (s, 3 H), 3.38 and 3.08 (ABX, JAB = 9.5, JAX = 6.2, JBX
= 4.4 Hz, 2 H), 3.22 and 3.00 (ABX, JAB = 9.7, JAX = 6.4, JBX
=
6.8 Hz, 2 H), 2.58 (d, J = 7.7 Hz, 2 H), 2.44 (s, 3 H), 2.31–2.17 (m,
3 H), 0.83 (d, J = 7.0 Hz, 3 H) ppm. 13C NMR (75 MHz, CDCl3):
δ = 158.0, 143.2, 134.3, 131.8, 129.5, 129.4, 127.3, 113.9, 55.2, 54.6,
50.8, 43.7, 35.3, 32.8, 21.5, 13.2 ppm. HRMS (EI): m/z calcd. for
C20H25NO3S [M+] 359.1555; found 359.1559.
5-Ethoxy-2,2-dimethyl-3-(thiophen-2-ylmethyl)tetrahydrofuran (2o):
Yield 22.1 mg (46%); white solid; Rf = 0.73 (hexane/EtOAc, 4:1).
1H NMR (300 MHz, CDCl3): δ = 7.12–7.11 (m, 1 H), 6.92–6.89
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