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Turova et al.
1.23—1.51 (m, 4 H, CH2CH2CH3); 2.59 (t, 2 H, C(O)CH2CH2,
J = 6.6 Hz); 3.21 (dt, 2 H, CH2(CH2)2CH3, J1 = 6.3 Hz,
J2 = 6.6 Hz); 3.33 (t, 2 H, C(O)CH2CH2, J = 6.4 Hz); 6.12 (br.s,
1 H, NH); 7.38—7.46 (m, 2 H, mꢀPh); 7.48—7.56 (m, 1 H,
pꢀPh); 7.94 (d, 2 H, oꢀPh, J = 7.7 Hz).
NHCH2CH2CH2); 1.92—2.05 (m, 2 H, PhCH2CH2CH2);
2.13—2.20 (m,
2 H, PhCH2CH2CH2); 2.66 (t, 2 H,
PhCH2CH2CH2, J = 7.5 Hz); 3.25 (q, 2 H, NHCH2, J = 6.6 Hz);
5.40 (br.s, 1 H, NH); 7.17—7.31 (m, 5 H, Ph).
NꢀtertꢀButylꢀ4ꢀphenylbutanamide (7c).24 A light yellow oil.
1H NMR (CDCl3), : 1.34 (s, 9 H, 3 CH3); 1.90—2.00 (m, 2 H,
PhCH2CH2CH2); 2,09 (t, 2 H, PhCH2CH2CH2, J = 7.3 Hz);
2.65 (t, 2 H, PhCH2CH2CH2, J = 7.3 Hz); 5.31 (br.s, 1 H, NH);
7.17—7.31 (m, 5 H, Ph).
NꢀtertꢀButylꢀ3ꢀbenzoylpropanamide (5c).16 White crystals,
m.p. 117.5—118.5 C (cf. Ref. 16: m.p. 116—117 C), the yield
1
was 2.80 g (60%). H NMR (CDCl3), : 1.32 (s, 9 H, 3 CH3);
2.53 (t, 2 H, C(O)CH2CH2, J = 6.6 Hz); 3.31 (t, 2 H,
C(O)CH2CH2, J = 6.4 Hz); 5.69 (br.s, 1 H, NH); 7.38—7.46
(m, 2 H, mꢀPh); 7.49—7.56 (m, 1 H, pꢀPh); 7.96 (d, 2 H, oꢀPh,
J = 7.3 Hz).
2ꢀtertꢀButylꢀ3ꢀmethylisoindolinꢀ1ꢀone (9).25 A light yellow
1
oil. H NMR (DMSOꢀd6), : 1.34 (s, 9 H, 3 CH3); 1.55—1.62
(m, 1 H, CH); 2.44 (s, 3 H, CH3); 7.47—7.58 (m, 4 H, Ph).
2ꢀAcetylꢀNꢀtertꢀbutylbenzamide (8).17 White crystals, m.p.
108.0—110.0 C (cf. Ref. 17: m.p. 115—116 C), the yield was
2.41 g (55%). 1H NMR (DMSOꢀd6), : 1.34 (s, 9 H, 3 CH3);
2.44 (s, 3 H, CH3); 7.47—7.58 (m, 4 H, Ph), 7.98 (br.s, 1 H, NH).
Hydrogenolysis of ꢀketo amides (general procedure). The catꢀ
alyst 1% Pd/sibunite (25 mg, 2.35•10–3 mgꢀat. of Pd) and an
amide (1, 5, or 8) (0.23 mmol) were placed into a preꢀevacuated
and filled with argon glass tube for hydrogenolysis, which was
again evacuated and filled with argon. Then, the solvent (2 mL)
and 1.47 M HCl/MeOH (if required) were added, the tube was
placed into a stainless steel autoclave (50 cm3) preliminary filled
with argon. The autoclave was purged with purified hydrogen,
and the H2 pressure was raised to 20 atm. Then, the reaction
mixture was magnetically stirred at a required temperature. After
completion of the experiment, the tube content was passed
through a layer of silica gel (1.5 cm) to remove the catalyst, using
ethyl acetate as an eluent, the solvents were evaporated. The
product obtained was analyzed by NMR.
1ꢀBenzylꢀ5ꢀmethylpyrrolidinꢀ2ꢀone (3a).18,19 A colorless oil.
1H NMR (CDCl3), : 1.05 (d, 3 H, CH3, J = 6.4 Hz); 1.41—1.55
(m, 1 H, C(O)CH2CHaHb); 1.97—2.12 (m, 1 H, C(O)CH2CHaHb);
2.20—2.46 (m, 2 H, C(O)CH2); 3.35—3.49 (sextet, 1 H, CH,
J = 6.4 Hz); 4.00 (d, 1 H, CHaHbPh, J = 14.7 Hz); 4.98 (d, 1 H,
CHaHbPh, J = 14.7 Hz); 7.10—7.25 (m, 5 H, Ph).
1ꢀ(4ꢀMethoxyphenyl)ꢀ5ꢀmethylpyrrolidinꢀ2ꢀone (3b).19 White
crystals, m.p. 58.0—60.0 C (cf. Ref. 19: m.p. 59—60 C).
1H NMR (CDCl3), : 1.17 (s, 3 H, CH3); 1.66—1.80 (m, 1 H,
C(O)CH2CHaHb); 2.31—2.38 (m, 1 H, C(O)CH2CHaHb);
2.49—2.67 (m, 2 H, C(O)CH2); 3.80 (s, 3 H, OCH3); 4.20 (m, 1 H,
NH); 6.91 (d, 2 H, Ph, J = 8.8 Hz); 7.16 (d, 2 H, Ph, J = 8.8 Hz).
5ꢀMethoxyꢀ1ꢀ(4ꢀmethoxyphenyl)ꢀ5ꢀmethylpyrrolidinꢀ2ꢀone
(4b). 1H NMR (CDCl3), : 1.35 (s, 3 H, CH3); 2.10—2.22 (m, 1 H,
C(O)CH2CHaHb); 2.27—2.43 (m, 1 H, C(O)CH2CHaHb);
2.46—2.63 (m, 2 H, C(O)CH2); 3.30 (s, 3 H, OCH3); 3.79 (s, 3 H,
ArOCH3); 6.91 (d, 2 H, Ph, J = 8.8 Hz); 7.16 (d, 2 H, Ph,
J = 8.8 Hz).
References
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NꢀBenzylꢀ4ꢀhydroxyꢀ4ꢀphenylbutanamide (6a).20 1H NMR
(CDCl3), : 1.95—2.09 (m, 2 H, C(O)CH2CH2); 2.26—2.34
(m, 2 H, C(O)CH2CH2); 4.35 (d, 2 H, CH2Ph, J = 5.9 Hz);
4.68—4.72 (m, 1 H, CH); 6.53 (br.s, 1 H, NH); 7.22—7.31
(m, 10 H, Ph).
NꢀBenzylꢀ4ꢀphenylbutanamide (7a).21 White crystals, m.p.
80.0—81.0 C (cf. Ref. 22: m.p. 83 C). 1H NMR (CDCl3),
: 1.95—2.09 (m, 2 H, PhCH2CH2CH2); 2.17—2.24 (m, 2 H,
PhCH2CH2CH2); 2.62—2.69 (m, 2 H, PhCH2CH2CH2); 4.40
(d, 2 H, CH2Ph, J = 5.8 Hz); 5.90 (br.s, 1 H, NH); 7.13—7.37
(m, 10 H, Ph).
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NꢀButylꢀ4ꢀphenylbutanamide (7b).23 A colorless oil. 1H NMR
(CDCl3), : 0.93 (t, 2 H, CH3, J = 7.3 Hz); 1.27—1.54 (m, 4 H,
Received February 25, 2015;
in revised form March 27, 2015