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2.1.6. (2R,3R)-2-Decyl-2-methyl-1-(4-methoxyphenyl)-3-
phenylaziridine (10b). Colorless oil (89%); IR (neat) 2926,
J¼14.5 Hz), 5.80 (1H, s). MS m/z (%) 285 (Mþ, 0.4), 271
(8), 226 (54), 184 (100), 131 (24), 88 (62), 60 (78). Calcd for
C16H31NO3: M, 285.2304. Found: m/z 285.2319.
1
2855, 1506, 1464, 1238 cm21; H NMR d 0.87 (3H, t, J¼
7 Hz), 1.07 (3H, s), 1.24–1.46 (18H, m), 3.09 (1H, s), 3.77
(3H, s), 6.79, 6.85 (each 2H, d, J¼9 Hz), 7.27–7.41 (5H,
m). MS m/z (%) 379 (Mþ, 73), 364 (4), 336 (3), 280 (22),
266 (87), 197 (100), 148 (62), 91 (76). Calcd for C26H37NO:
M, 379.2875. Found: m/z 379.2881. [a]2D9¼292.8 (c 0.5
acetone).
2.1.9. (S)-3-Acetamino-3-methyltridecanoic acid N-{1-
(1-naphthyl)ethyl}amide (18a). To a solution of 11a
(28.5 mg; 0.1 mmol) in CH2Cl2 (4 mL), EDC (23 mg;
0.12 mmol) and HOBt (16.4 mg; 0.12 mmol) were added
at 08C with stirring. After stirring for 1 h at 08C, (S)-(2)-1-
(1-naphthyl)ethylamine (32 mL; 0.2 mmol) was added to
the reaction mixture and stirred for 3 h. The reaction
mixture was washed with 5% aq. HCl twice and sat. aq.
NaHCO3 then dried over MgSO4. The solvent was
evaporated under vacuum to afford 43 mg (98%) of pure
18a as colorless oil; IR (neat) 3298, 3053, 2926, 2854, 1652,
2.1.7. N-(1-Benzyl-1-methylundecyl)acetamide (17a,b).
Palladium hydroxide (20 wt% Pd (dry basis) on carbon;
3.05 g, 300 wt%) was added to a solution of 10a (1.05 g;
2.77 mmol) in 50 mL of a mixture of MeOH and AcOEt.
The reaction mixture was stirred for 30–60 min under
hydrogen atmosphere. The catalyst was filtered off and
the solvent was evaporated under vacuum to afford the
secondary amine 15a. Without further purification, a
solution of CAN (6.07 g; 11.1 mmol) in 13 mL of water
was added to a solution of 15a in 25 mL of CH3CN at 08C
with stirring. The reaction mixture was stirred at 08C for
30 min, then the solution was neutralized with 5% aq.
NaHCO3. Na2SO3 (1.4 g) was added to the reaction mixture
with stirring and after 10 min, the reaction mixture was
filtered through a celite pad. The aqueous layer was
extracted with AcOEt. The combined organic layers were
washed with sat. aq. NaHCO3, 10% aq. Na2SO3, and brine,
and then dried over MgSO4. After concentration, obtained
crude 16a was successively added pyridine (11 mL), acetic
anhydride (5.2 mL) and 4-(dimethylamino)pyridine (67 mg;
0.55 mmol). The reaction mixture was stirred at room
temperature for 1 h. The acetic anhydride and pyridine were
evaporated under vacuum and the residue was purified by
silica gel column chromatography to give (S)-(þ)-17a
(412 mg; 47% from 10a) as colorless oil; IR (neat) 3298,
2925, 2855, 1652, 1558, 1465, 1371, 1031 cm21; [a]D29¼
þ28.9 (c 0.5 acetone).
1
1525, 1449, 1372, 799, 778, 756 cm21; H NMR d 0.87
(3H, t, J¼7 Hz), 1.15 (3H, s), 1.10–1.31 (18H, m), 1.34
(3H, s), 1.65 (3H, d, J¼6.7 Hz), 2.28, 2.89 (each 1H, d,
J¼12.8 Hz), 5.41 (1H, s), 5.95–6.01 (1H, m), 6.09 (1H, d,
J¼8.9 Hz), 7.12–8.17 (7H, m). MS m/z (%) 438 (Mþ, 28),
268 (35), 209 (11), 170 (100), 155 (54). Calcd for
C28H42N2O2: M, 438.3246. Found: m/z 438. 3249.
[a]2D5¼22.4 (c 0.73 acetone).
2.1.10. (R)-3-Acetamino-3-methyltridecanoic acid N-{1-
(1-naphthyl)ethyl}amide (18b). Colorless oil (94%); IR
(neat) 3299, 3053, 2927, 2855, 1645, 1525, 1449, 1372,
1239, 799, 777, 756 cm21; 1H NMR d 0.88 (3H, t, J¼7 Hz),
1.26–1.40 (18H, m), 1.32 (3H, s), 1.46 (3H, s), 1.63 (3H, d,
J¼6.7 Hz), 2.55, 2.60 (each 1H, d, J¼13 Hz), 5.68 (1H, s),
5.92–5.98 (1H, m), 6.11 (1H, d, J¼8.6 Hz), 7.43–8.13 (7H,
m). MS m/z (%) 438 (Mþ, 26), 268 (34), 209 (11), 170
(100), 155 (54). Calcd for C28H42N2O2: M, 438.3246.
Found: m/z 438.3250. [a]2D1¼21.6 (c 0.7 acetone).
2.1.11. (dl)-2-Acetamino-2-methyldodecanoic acid
(19a,b). Colorless crystals (14%); IR (KBr) 3339, 2921,
2851, 2604, 1701, 1631, 1555, 1469, 1372, 1326, 1254,
1
Compound (R)-(2)-17b. Colorless oil (31% yield);
[a]3D0¼230.9 (c 0.5 acetone). Racemic-17: Colorless
crystals; mp 82–838C (AcOEt–hexane). IR (KBr) 3277,
3088, 2918, 2848, 1643, 1568, 1470, 1371 cm21; 1H NMR d
0.88 (3H, t, J¼7 Hz), 1.19 (3H, s), 1.26–1.55 (17H, m), 1.51
(1H, m), 1.91 (3H, s), 2.89, 3.19 (each 1H, d, J¼13 Hz),
4.86 (1H,s), 7.12–7.29 (5H, m). MS m/z (%) 317 (Mþ, 3),
302 (5), 274 (0.5), 258 (6), 226 (60), 184 (100), 176 (6), 134
(6), 91 (11), 70 (7). Calcd for C21H35NO: M, 317.2719.
Found: m/z 317.2715. Anal. calcd for C21H35NO: C, 79.43;
H, 11.12; N, 4.41. Found: C, 79.27; H, 11.08; N, 4.35.
1238, 1143 cm21; H NMR d 0.88 (3H, t, J¼7 Hz), 1.10–
1.32 (16H, m), 1.58 (3H, s), 1.84 (1H, m), 2.04 (3H, s), 2.14
(1H, m), 6.07 (1H, s). MS m/z (%) 271 (Mþ, 5), 226 (52),
184 (100), 144 (22), 130 (19), 113 (15), 102 (30), 88 (50), 60
(71). Calcd for C15H29NO3: M, 271.2147. Found: m/z
271.2141.
2.1.12. (2S,3R)-2-Decyl-1-(4-methoxyphenyl)-3-phenyl-
aziridine (20a). To a solution of EtMgBr (2.07 mmol) in
20 mL of THF at 2788C was added a solution of 8a
(300 mg; 0.59 mmol) in 4 mL of THF dropwise with
stirring. After 10 min, the cooling bath was removed and
the reaction mixture was allowed to warm up to room
temperature at once and was stirred at room temperature for
30 min. The reaction was quenched by sat. aq. NH4Cl and
the whole was extracted with CHCl3. The organic layer was
washed once with sat. aq. NH4Cl and dried over MgSO4.
The product was purified by silica gel flash chromatography
to afford 20a (210 mg; 97%) as colorless oil; IR (neat) 2924,
2854, 1506, 1464, 1455, 1241, 1180, 1041 cm21; 1H NMR d
0.87 (3H, t, J¼7 Hz), 1.21–1.53 (18H, m), 1.56 (3H, s), 2.35
(1H, dt, J¼6.4, 6.7 Hz), 3.24 (1H, d, J¼6.4 Hz), 3.76 (3H,
s), 6.79, 6.96 (each 2H, d, J¼8.8 Hz), 7.27–7.42 (5H, m).
MS m/z (%) 365 (Mþ, 100), 308 (7), 294 (11), 274 (25), 252
(94), 238 (40), 224 (22), 211 (31), 197 (21), 162 (5), 134
2.1.8. 3-Acetamino-3-methyltridecanoic acid (11a,b). A
mixture of 17a (50 mg; 0.16 mmol), ruthenium trichloride
hydrate (1.6 mg; 0.00785 mmol) and sodium periodate
(600 mg; 2.82 mmol) in a mixture of CCl4 (1.5 mL),
CH3CN (1.5 mL) and water (1 mL) was stirred at room
temperature for 2 days. The mixture was extracted with
AcOEt and the organic layer was washed with brine and
then dried over MgSO4. After concentration, the residue
was purified by silica gel column chromatography to give
11a (16.6 mg; 37%) as colorless oil; IR (neat) 3335, 2926,
2855, 1714, 1659, 1549, 1466, 1376, 1221 cm21; 1H NMR d
0.88 (3H, t, J¼7 Hz), 1.25–1.29 (16H, m), 1.38 (3H, s),
1.70, 1.85 (each 1H, m), 1.95 (3H, s), 2.65, 2.91 (each 1H, d,