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17 Spectral data for compound 5a (major isomer): white solid, mp 70-71 °C; [α]D
25 +6.0
(c 2.0, CHCl3). IR (CH2Cl2):
3437, 3069, 3037, 2988, 2890, 1731, 1616, 1502, 1461, 1257, 1208,
1176 cm-1. 1H NMR
(300 MHz, CDCl3): δ = 1.34 (s, 3 H,
CH3), 1.38 (s, 3 H, CH3), 1.89-2.00
(m, 1 H, CH2
CH
2
CHN), 2.07-2.19 (m, 1
H, CH2
CH
2
CHN),
2.50-2.61 (m, 2 H, CH
2
CH2CO), 2.65-2.71
(m, 1 H, CH2
CHN), 3.61 (s,
CO2
CH
3
),
3.74-3.81 [dd, 1 H, J = 7.4
Hz and J = 8.2 Hz, CH
2
(OC)CH(OC)CHN],
3.80 (d, 1 H, J = 13.4
Hz, NCH
2
Ph),
3.85 (d, 1 H, J = 13.4
Hz, NCH
2
Ph),
4.09-4.14 [m, 1 H, J = 6.4
Hz and J = 8.2
Hz, CH
2
(OC)CH(OC)CHN], 4.30-4.37 [m,
1 H, CH2(OC)CH(OC)CHN],
5.39 (br s, 1 H, NOH), 7.26-7.30 (m, 5 H, CHarom.). 13C
NMR (75 MHz, CDCl3): δ = 22.13 (CH2
CH
2
CHN),
25.35 (CH
3
CCH3),
26.43 (CH3CCH
3
), 31.53 (CH2
CH
2
CO),
51.42 (CO2
CH
3
), 60.33 (NCH
2
Ph), 67.45 [CHN(OH)Bn], 68.63 [CH
2
(OC)CH(OC)CHN],
75.37 [CH2(OC)CH(OC)CHN], 108.67
(CH3
CCH3), 127.15,
128.17 and 129.09 (5 × CH
arom.),
138.10 (C
arom.), 174.64 (C=O). LRMS (DCI): m/z = 324 [(M + H)+],
322.1, 308.2, 220.2. Anal. Calcd for C18H27NO5:
C, 63.14; H, 7.79; N, 4.33. Found: C, 63.17; H, 7.82; N, 4.33.
18a
Girard P.
Namy JL.
Kagan HB.
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1980,
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18b
Kagan HB.
Namy JL.
Girard P.
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1981,
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18c
Hasegawa E.
Curran DP.
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19 Transformation of 5a to
compound 6: To a solution of compound 5a (0.130 g, 0.403 mmol) in THF (100 mL)
were added di-tert-butyl dicarbonate
(0.100 g, 0.458 mmol) and Raney-Ni (0.510 g). This suspension was
stirred under H2 (35 bar) at 60 °C
overnight, and then the reaction mixture was filtered through celite.
The filtrate was concentrated in vacuo and purified by chromatography
on silica gel to afford compound 6 (0.090
g, 82%), which exhibited spectral data in agreement with
ref.
[7]
: mp 85-86 °C,
lit: 79-80 °C; [α]D
25
-16.0
(c 1.6, CHCl3), lit : [α]D
20 -16.0
(c 1, CHCl3). Anal. Calcd
for C15H27NO6: C, 56.77; H, 8.57;
N, 4.41. Found: C, 56.71; H, 8.77; N, 4.33.
20
Merino P.
Castillo E.
Franco S.
Merchan FL.
Tejero T.
Tetrahedron:
Asymmetry
1998,
9:
1759
