EPOXY DERIVATIVES OF {(5-[(1-PHENYLETHYL)AMINOCARBONYL]CYCLOPENT-...
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added, and the mixture was stirred for 5 h (TLC). The
mixture was evaporated under reduced pressure, and
the residue was subjected to chromatography on silica
gel using petroleum ether–ethyl acetate (1:1) as eluent.
Yield 450 mg (98%), colorless crystals, mp 97–99°C,
[α]D20 = –56.2° (c = 1.0, CHCl3). IR spectrum, ν, cm–1:
3325 (NH), 2962, 2860, 1739 (C=O), 1641 (C=O),
ene chloride. The mixture was stirred for 8 h at room
temperature (TLC), washed with 15 ml of a saturated
solution of Na2S2O3 and 15 ml of a 5% aqueous solu-
tion of NaHCO3, dried over MgSO4, and evaporated
under reduced pressure. The residue was subjected to
chromatography on silica gel using petroleum ether–
ethyl acetate (1:1) as eluent.
1
1525, 1454, 1377, 1236, 1033, 702. H NMR spec-
{(1S,2R,3S,5R)-3-{[(1R)-Phenylethyl]aminocar-
bonyl}-6-oxabicyclo[3.1.0]hex-2-yl}methyl acetate
(V). Yield 163 mg (48%), colorless crystals, mp 95–
97°C, [α]D20 = +49.9° (c = 0.875, CHCl3). IR spectrum,
ν, cm–1: 3288 (NH), 2953, 2924, 2852, 1735 (C=O),
1645 (C=O), 1521, 1458, 1377, 1240, 1037, 854, 704.
1H NMR spectrum, δ, ppm: 1.45 d (3H, CH3CH, J =
6.6 Hz), 1.98 s (3H, CH3CO), 2.22 d.d.d (1H, 4-H,
J = 1.25, 10.2, 14.0 Hz), 2.34 d.d (1H, 4-H, J = 1.2,
14.2 Hz), 2.71 t.d (1H, 3-H, J = 6.3, 10.2 Hz), 3.03 t.d
(1H, 2-H, J = 1.5, 10.5 Hz), 3.47–3.59 m (1H, 5-H),
3.60–3.67 m (1H, 1-H), 4.01 d.d (1H, CH2O, J = 9.1,
11.2 Hz), 4.14 d.d (1H, CH2O, J = 6.4, 10.4 Hz),
4.99 quintet (1H, CHPh, J = 6.95 Hz), 7.20–7.36 m
(5H, Ph), 7.50 d (1H, NH, J = 6.95 Hz). 13C NMR
spectrum, δC, ppm: 20.6 (CH3CO), 21.9 (CH3CH),
32.3 (C4), 42.6 (C3), 44.2 (C2), 48.8 (CHPh), 57.7 (C5),
59.5 (C1), 61.9 (CH2O), 126.1, 127.1, 128.6 (Ph),
143.2 (Ph), 170.3 (COCH3), 171.9 (CON). Mass spec-
trum (APCI), m/z (Irel, %): 304 [M + H]+ (100),
244 (46.8). Found, %: C 67.24; H 6.55; N 4.27.
C17H21NO4. Calculated, %: C 67.33; H 6.93; N 4.62.
trum, δ, ppm: 1.50 d (3H, CH3CH, J = 5.7 Hz), 1.99 s
(3H, CH3CO), 2.38–2.48 m (1H, 4-H, J = 5.7 Hz),
2.71–2.82 m (1H, 4-H), 3.04 q (1H, 5-H, J = 9.1 Hz),
3.10–3.23 m (1H, 1-H), 4.05 d.d (1H, CH2O, J = 5.7,
11.6 Hz), 4.20 d.d (1H, CH2O, J = 5.8, 11.8 Hz),
5.13 quint (1H, CHPh, J = 7.05), 5.58–5.64 m (1H,
3-H), 5.80–5.87 m (1H, 2-H), 5.99–6.13 br.s (1H, NH),
7.20–7.36 m (5H, Ph). 13C NMR spectrum, δC, ppm:
20.7 (CH3CO), 21.6 (CH3CH), 35.1 (C4), 46.1 (C1),
47.3 (C5), 48.7 (CHPh), 64.9 (CH2O), 126.2, 127.2,
128.6 (Ph), 129.8 (C3), 131.7 (C2), 143.1 (Ph), 170.7
(COCH3), 171.4 (CON). Mass spectrum (APCI), m/z
(Irel, %): 288 [M + H]+ (100), 228 (91.5), 125 (2.1), 93
(2.0). Found, %: C 70.94; H 7.55; N 4.69. C17H21NO3.
Calculated, %: C 71.08; H 7.32; N 4.88.
[(1S,5R)-5-{[(1R)-1-phenylethyl]aminocarbonyl}-
cyclopent-2-en-1-yl]methyl acetate (IVb) was syn-
thesized in a similar way from 350 mg (1.4 mmol) of
hydroxy amide IIIb. Yield 393 mg (98%), colorless
crystals, mp 103–105°C, [α]D20 = +135.6° (c = 1.075,
CHCl3). IR spectrum, ν, cm–1: 3292 (NH), 2953, 2852,
1728 (C=O), 1639 (C=O), 1548, 1456, 1377, 1255,
1240, 1041, 759, 719, 698. 1H NMR spectrum, δ, ppm:
1.50 d (3H, CH3CH, J = 4.76 Hz), 1.85 s (3H,
CH3CO), 2.46–2.56 d.d (1H, 4-H, J = 15.4, 5.48 Hz),
2.72–2.82 m (1H, 4-H), 3.05 q (1H, 5-H, J = 7.1 Hz),
3.13–3.21 m (1H, 1-H), 4.00 d.d (1H, CH2O, J = 6.4,
11.6 Hz), 4.11 d.d (1H, CH2O, J = 6.4, 11.8 Hz),
5.14 quint (1H, CHPh, J = 7.15 Hz), 5.58–5.63 m (1H,
3-H), 5.83–5.86 m (1H, 2-H), 5.91–5.96 br.s (1H, NH),
7.23–7.37 m (5H, Ph). 13C NMR spectrum, δC, ppm:
20.7 (CH3CO), 21.8 (CH3CH), 35.4 (C4), 46.2 (C1),
47.2 (C5), 48.8 (CHPh), 64.2 (CH2O), 126.2, 127.3,
128.6 (Ph), 129.9 (C3), 131.6 (C2), 143.1 (Ph), 170.7
(COCH3), 171.5 (CON). Mass spectrum (APCI), m/z
(Irel, %): 288 [M + H]+ (100), 228 (73.5), 125 (4.3), 93
(3.6). Found, %: C 71.02; H 7.15; N 4.71. C17H21NO3.
Calculated, %: C 71.08; H 7.32; N 4.88.
{(1R,2R,3S,5S)-3-{[(1R)-Phenylethyl]aminocar-
bonyl}-6-oxabicyclo[3.1.0]hex-2-yl}methyl acetate
(VI). Yield 140 mg (42%), colorless crystals, mp 167–
169°C, [α]D20 = –14.1° (c = 0.871, CHCl3). IR spectrum,
ν, cm–1: 3298 (NH), 2953, 2924, 2852, 1743 (C=O),
1643 (C=O), 1554, 1458, 1377, 1228, 1041, 840, 700.
1H NMR spectrum, δ, ppm: 1.50 d (3H, CH3CH, J =
6.95 Hz), 2.04 s (3H, CH3CO), 2.18 d.d.d (1H, 4-H,
J = 1.2, 10.2, 16.1 Hz), 2.28 d.d (1H, 4-H, J = 1.8,
16.2 Hz), 2.57 t.d (1H, 3-H, J = 6.6, 9.1 Hz), 2.73 t.d
(1H, 2-H, J = 2.1, 9.9 Hz), 3.44–3.55 m (2H, 5-H,
1-H), 3.97 d.d (1H, CH2O, J = 8.3, 11.6 Hz), 4.23 d.d
(1H, CH2O, J = 6.3, 11.5 Hz), 5.11 quint (1H, CHPh,
J = 6.95 Hz), 5.87–6.00 br.s (1H, NH), 7.23–7.36 m
(5H, Ph). 13C NMR spectrum, δC, ppm: 22.8 (CH3CO),
23.6 (CH3CH), 30.9 (C4), 42.2 (C3), 41.3 (C2), 50.0
(CHPh), 56.9 (C5), 58.3 (C1), 62.5 (CH2O), 124.5,
125.8, 127.0 (Ph), 143.5 (Ph), 169.6 (COCH3), 170.3
(CON). Mass spectrum (APCI), m/z (Irel, %): 304
[M + H]+ (100), 244 (83.2). Found, %: C 66.99;
H 6.67; N 4.35. C17H21NO4. Calculated, %: C 67.33;
H 6.93; N 4.62.
Compounds V and VI. A solution of 572 mg
(3.3 mmol) of m-chloroperoxybenzoic acid and
272 mg (3.3 mmol) of sodium hydrogen carbonate in
10 ml of methylene chloride was added to a solution of
317 mg (1.3 mmol) of acetate IVa in 10 ml of methyl-
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY Vol. 46 No. 4 2010