1030
Z. Huang et al.
LETTER
(m, 2 H), 7.22–7.18 (m, 2 H), 6.10 (br s, 1 H), 4.64 (d, J = 5.7
Hz, 2 H), 2.47 (s, 3 H). 13C NMR (75 MHz, CDCl3): d =
169.8, 138.1, 136.2, 136.2, 131.0, 129.9, 128.8, 127.8,
127.6, 126.6, 125.7, 43.9, 19.8. APCI-MS: m/z = 226 [M+].
N-Benzyl-3-cyanobenzamide (Table 3, Entry 6): 1H NMR
(300 MHz, CDCl3): d = 8.08 (s, 1 H), 8.07 (d, J = 8.1 Hz, 2
H), 8.03 (d, J = 7.9 Hz, 1 H), 7.79 (t, J = 7.5 Hz, 1 H), 7.37–
References and Notes
(1) (a) Smith, M. B.; March, J. March’s Advanced Organic
Chemistry, 5th ed.; John Wiley and Sons, Inc.: New York,
NY, 2001, Chap. 10, 512. (b) Druzian, J.; Zucco, C.;
Rezende, M. C.; Nome, F. J. Org. Chem. 1989, 54, 4767.
(c) Deshpande, M. S. Tetrahedron Lett. 1994, 35, 5613.
(2) (a) Pelter, A.; Levitt, T. E.; Nelson, P. Tetrahedron 1970, 26,
1539. (b) Pelter, A.; Levitt, T. E.; Nelson, P. Tetrahedron
1970, 26, 1545.
7.33 (m, 5 H), 6.47 (br s, 1 H), 4.65 (d, J = 5.6 Hz, 2 H). 13
NMR (125 MHz, CDCl3): d = 165.1, 137.5, 135.6, 134.7,
C
131.2, 130.7, 129.6, 128.9, 128.0, 127.9, 117.9, 113.0, 44.4.
APCI-MS: m/z = 237 [M+].
(3) Collum, D. B.; Chen, S.; Ganem, B. J. Org. Chem. 1978, 43,
4393.
N,N-Diphenylacetamide (Table 3, Entry 7): 1H NMR (300
MHz, CDCl3): d = 7.36–7.28 (m, 10 H), 2.05 (s, 3 H). 13
C
(4) (a) Ishihara, K.; Ohara, S.; Yamamoto, H. J. Org. Chem.
1996, 61, 4196. (b) Maki, T.; Ishihara, K.; Yamamoto, H.
Synlett 2004, 1355. (c) Maki, T.; Ishihara, K.; Yamamoto,
H. Org. Lett. 2005, 7, 5043. (d) Maki, T.; Ishihara, K.;
Yamamoto, H. Org. Lett. 2005, 7, 5047. (e) Maki, T.;
Ishihara, K.; Yamamoto, H. Org. Lett. 2006, 8, 1431.
(5) Houston, T. A.; Wilkinson, B. L.; Blanchfield, J. T. Org.
Lett. 2004, 6, 679.
NMR (125 MHz, CDCl3): d = 170.4, 129.6, 128.9, 126.4,
23.8. APCI-MS: m/z = 212 [M+].
N¢-(Cyclohexanecarbonyl)-4-methylbenzenesulfono-
hydrazide (Table 3, Entry 8): 1H NMR (500 MHz, CDCl3):
d = 7.78 (d, J = 8.2 Hz, 2 H), 7.52 (d, J = 6.0 Hz, 1 H), 7.30
(d, J = 8.0 Hz, 2 H), 7.23 (d, J = 6.2 Hz, 1 H), 2.42 (s, 3 H),
1.99–1.97 (m, 1 H), 1.70–1.68 (m, 2 H), 1.63–1.60 (m, 3 H),
1.21–1.13 (m, 5 H). 13C NMR (75 MHz, CDCl3): d = 174.0,
144.8, 133.0, 129.4, 128.7, 43.0, 28.9, 25.3, 25.2, 21.7.
APCI-MS: m/z = 297 [M+].
(6) Brown, H. C.; Stocky, T. P. J. Am. Chem. Soc. 1977, 99,
8218.
(7) General Procedure for Formation of Amides and Esters:
To a carboxylic acid (1–2 mmol) in toluene (10 mL) was
added a solution of borane–THF (1 M) in THF in an ice bath.
The mixture was warmed to r.t. for 1 h. An amine or an
alcohol was added and the mixture was heated at reflux for
12 h or 24 h. The resulting mixture was cooled to r.t. and
treated with HCl (1 M), and then diluted with EtOAc (20
mL). The organic phase was washed with H2O and
concentrated under reduced pressure and purified by flash
chromatography. The physical data of compounds are
provided below.
(8) Methyl 2-Hydroxy-2-phenylacetate (Table 4, Entry 1):
1H NMR (300 MHz, CDCl3): d = 7.41–7.34 (m, 5 H), 5.19
(d, J = 5.6 Hz, 1 H), 3.76 (s, 3 H), 3.44 (d, J = 5.6 Hz, 1 H).
13C NMR (125 MHz, CDCl3): d = 174.1, 138.2, 128.6, 126.6,
120.0, 72.9, 53.0.
Butyl Hexanoate (Table 4, Entry 2): 1H NMR (300 MHz,
CDCl3): d = 4.09 (t, J = 6.6 Hz, 2 H), 2.31 (t, J = 7.4 Hz, 2
H), 1.63–1.60 (m, 4 H), 1.36–1.30 (m, 6 H), 0.95–0.87 (m, 6
H). 13C NMR (125 MHz, CDCl3): d = 174.0, 64.1, 34.3, 31.3,
30.7, 24.7, 22.3, 19.1, 13.9, 13.7.
N-Butylhexanamide (Table 3, Entry 1): 1H NMR (500
MHz, CDCl3): d = 5.37 (br s, 1 H), 3.25 (t, J = 7.0 Hz, 2 H),
2.14 (t, J = 8.0 Hz, 2 H), 1.64–1.60 (m, 2 H), 1.47–1.46 (m,
2 H), 1.36–1.30 (m, 6 H), 0.94–0.88 (m, 6 H). 13C NMR (125
MHz, CDCl3): d = 170.6, 36.8, 34.5, 29.4, 29.1, 23.1, 20.0,
17.7, 11.5, 11.4. APCI-MS: m/z = 172 [M+].
4-Bromophenyl Acetate (Table 4, Entry 3): 1H NMR (500
MHz, CDCl3): d = 7.50 (d, J = 6.7 Hz, 2 H), 7.00 (d, J = 6.7
Hz, 2 H), 2.29 (s, 3 H). 13C NMR (125 MHz, CDCl3): d =
169.1, 149.6, 132.4, 123.3, 118.9, 21.0.
4-Methoxyphenyl Acetate (Table 4, Entry 4): 1H NMR
(300 MHz, CDCl3): d = 7.01 (d, J = 6.7 Hz, 2 H), 6.90 (d,
J = 6.7 Hz, 2 H), 3.79 (s, 3 H), 2.28 (s, 3 H). 13C NMR (125
MHz, CDCl3): d = 169.1, 157.2, 144.2, 122.3, 114.4, 55.5,
21.0.
1-Morpholinononan-1-one (Table 3, Entry 2): 1H NMR
(500 MHz, CDCl3): d = 3.68–3.61 (m, 6 H), 3.48–3.44 (m, 2
H), 2.33–2.28 (m, 2 H), 1.62–1.55 (m, 2 H), 1.30–1.27 (m,
10 H), 0.90–0.85 (m, 3 H). 13C NMR (125 MHz, CDCl3):
d = 171.9, 66.9, 66.7, 46.0, 41.8, 33.1, 31.8, 29.4, 29.3, 29.1,
25.2, 22.6, 14.0. APCI-MS: m/z 228 [M+].
4-Cyanophenyl Acetate (Table 4, Entry 5): 1H NMR (300
MHz, CDCl3): d = 7.71 (d, J = 8.8 Hz, 2 H), 7.26 (d, J = 8.8
Hz, 2 H), 2.33 (s, 3 H). 13C NMR (125 MHz, CDCl3): d =
168.4, 153.9, 133.6, 122.7, 118.2, 109.7, 21.1.
N-Benzylcyclohexanecarboxamide (Table 3, Entry 3): 1H
NMR (500 MHz, CDCl3): d = 7.34–7.26 (m, 5 H), 5.70 (br
s, 1 H), 4.44 (d, J = 5.6 Hz, 2 H), 2.16–2.05 (m, 1 H), 1.90–
1.87 (m, 2 H), 1.80–1.78 (m, 2 H), 1.60–1.59 (m, 1 H), 1.47–
1.45 (m, 2 H), 1.28–1.22 (m, 3 H). 13C NMR (75 MHz,
CDCl3): d = 175.8, 138.5, 128.7, 127.7, 127.4, 45.6, 43.4,
29.7, 25.7. APCI-MS: m/z 218 [M+].
4-Bromophenyl Cyclohexanecarboxylate (Table 4, Entry
6): 1H NMR (300 MHz, CDCl3): d = 7.48 (d, J = 6.7 Hz, 2
H), 6.96 (d, J = 6.7 Hz, 2 H), 2.58–2.51 (m, 1 H), 2.08–2.00
(m, 2 H), 1.88–1.80 (m, 2 H), 1.74–1.50 (m, 3 H), 1.47–1.37
(m, 3 H). 13C NMR (125 MHz, CDCl3): d = 174.2, 149.9,
132.3, 123.3, 118.6, 43.1, 28.9, 25.6, 25.3.
2-{[(Benzyloxy)carbonyl]methyl}benzoic Acid (Table 4,
Entry 7): 1H NMR (300 MHz, CDCl3): d = 8.15 (d, J = 7.7
Hz, 1 H), 7.55 (t, J = 6.1 Hz, 1 H), 7.44 (t, J = 8.5 Hz, 1 H),
7.34–7.28 (m, 6 H), 5.15 (s, 2 H), 4.11 (s, 2 H). 13C NMR
(125 MHz, CDCl3): d = 171.3, 136.7, 135.9, 133.3, 132.4,
131.9, 128.5, 128.2, 128.1, 127.6, 66.6, 40.7. APCI-MS:
m/z = 269 [M–].
N-Benzyl-4-methylbenzamide (Table 3, Entry 4):2 1
H
NMR (500 MHz, CDCl3): d = 7.69 (d, J = 8.1 Hz, 2 H), 7.36
(d, J = 4.3 Hz, 4 H), 7.31–7.33 (m, 1 H), 7.23–7.22 (m, 2 H),
6.32 (br s, 1 H), 4.65 (d, J = 5.6 Hz, 2 H), 2.39 (s, 3 H). 13
NMR (125 MHz, CDCl3): d = 167.2, 141.9, 138.3, 131.5,
C
129.2, 128.7, 127.9, 127.6, 126.9, 44.1, 21.4. APCI-MS:
m/z = 226 [M+].
N-Benzyl-2-methylbenzamide (Table 3, Entry 5): 1H
NMR (500 MHz, CDCl3) d = 7.38–7.35 (m, 5 H), 7.32–7.28
Synlett 2007, No. 7, 1026–1030 © Thieme Stuttgart · New York