A Route to Carbasugar Analogues - Jonathan Clayden - The ...

Experimental for chapter 3.2
324.1958; IR ν max (film)/cm⎯¹ 3315 (br, O-H), 2931 (C-H), 1641 (C=O), 1534 (N-H);
¹H-NMR (CDCl 3 , 500 MHz) δ 7.25-7.23 (m, 10H, Ph), 6.32 (d, 1H, J 7.5, NH), 5.23
(dd, 1H, J 8.0, 4.5, CHNPh), 4.30 (d, 1H, J 4.5, CHOPh), 2.09 (tt, 1H, J 11.5, 3.0,
CH), 1.81-1.71 (m, 4H), 1.67-1.61 (m, 1H), 1.36-1.15 (m, 5H); ¹³C-NMR (CDCl 3 , 125
MHz) δ 176.4 (C=N), 140.7 (ipso-Ph), 139.6 (ipso-Ph), 128.7, 128.2 (Ph), 127.7 (para-
Ph), 127.7 (para-Ph), 126.8, 126 (Ph), 77.2 (CHOPh), 59 (CHNPh), 45.4 (CH), 29.6,
29.4, 25.6, 25.6 (CH 2 ).
Synthesis of (3S*,4S*)-N-((S*)-1,2-diphenylethyl)-3-isopropyl-4-methylcyclohexanone-4-carboxamide
(206)
Ph
O
N
Ph
H 2 Pd/C 20 bar
Ph
Ph
H
N
O
O
O
A solution of oxazoline 201 (90 mg, 0.24 mmol) in methanol (6 cm 3 ) was passed
thorough the H-cube (1 cm 3 /min, 20 bar, Pd/C) and the eluent collected for 30 min.
The solvent was removed by rotary evaporation to give amide 206 (93 mg, 96%) as a
colourless oil.
R f : 0.10 (4:1, petrol:EtOAc); MS m/z (CI+) 378 (100%, MH + ), 379 (24%, (M+1)H + );
HRMS: found 378.2425, MH requires 378.2428; IR ν max (film)/cm⎯¹ 2932 (m, C-H),
1714 (ketone), 1639 (amide), 1531 (m, N-H), 1453 (m); ¹H-NMR (CDCl 3 , 500 MHz)
δ 7.37-7.18 (m, 8H, Ph), 7.11-7.16 (m, 2H, Ph), 5.93 (br d, 1H, J 8.0, NH), 5.39-5.29
(m, 1H, CHNPh), 3.23 (dd, 1H, J 14.0, 6.0, CH 2 Ph), 3.02 (dd, 1H, J 14.0, 9.0, CH 2 Ph),
2.96-2.85 (m, 1H), 2.93 (dd, 1H, J 14.5, 12.0), 2.74 (ddd, 1H, J 15.5, 11.5, 6.5), 2.17-
2.11 (m, 2H), 1.82-1.75 (m, 2H, CHMe 2 , CH), 1.59-1.53 (m, 2H), 1.20 (s, 3H, J 6.5,
Me), 0.81 (d, 3H, J 6.5, i-Pr), 0.52 (d, 3H, i-Pr); ¹³C-NMR (CDCl 3 , 75.5 MHz) δ
213.4, 174.5, 141.5, 137.3, 129.2, 128.6, 128.4, 127.5, 126.7, 126.5, 53.7, 51.8, 43.2,
42.7, 38.3, 38.1, 37.0, 27.7, 24.5, 23.7, 17.2.
237