4724
J. Granander et al. / Tetrahedron 58 *2002) 4717±4725
9.0 Hz, 1H, PhCHCH2), 3.45±3.58 ,m, 3H, PhCHCH2 and
CH3CH2O), 3.99 ,dd, J3.8, 9.0 Hz, 1H, PhCHCH2), 7.23±
7.27 ,m, 1H, Ph), 7.30±7.34 ,m, 2H, Ph), 7.38±7.41 ,m, 2H,
,CH3)2CHN), 1.26 ,t, J6.8 Hz, 3H, CH3CH2O), 2.82 ,m,
2H, ,PhCH2), 2.99 ,sept., J6.4 Hz, 1H, ,CH3)2CHN), 3.08
,m, 1H, PhCH2CHCH2), 3.34 ,m, 2H, PhCH2CHCH2), 3.52
,m, 2H, CH3CH2O), 7.22±7.32 ,m, 3H, Ph), 7.33±7.39 ,m,
20
Ph); [a]D 173.5 ,c 3.0, ethanol); nmax ,liquid ®lm) 3340,
20
1109 cm21
C15H26NO requires 236.2014.
;
HRMS ,FAB): MH1, found 236.2052.
2H, Ph); [a]D 113.8 ,c 3.1, ethanol); nmax ,liquid ®lm)
3322, 1113 cm21; HRMS ,FAB): MH1, found 222.1873.
C14H24NO requires 222.1858.
4.7.8. /S)-N-Cyclohexyl-O-methylphenylglycinol /2g).
Colorless oil ,80%); H NMR ,400 MHz, CDCl3) d 0.98±
1
4.7.14. /S)-N-Isopropyl-O-isopropylphenylalaninol /3c).
Colorless oil ,10%); H NMR ,400 MHz, CDCl3) d 0.99
1
1.18 ,m, 5H, ,CH2)5CHN), 1.54 ,m, 1H, ,CH2)5CHN),
1.62±1.73 ,m, 3H, ,CH2)5CHN), 2.02 ,m, 1H,
,CH2)5CHN), 2.28 ,m, 1H, ,CH2)5CHN), 3.36 ,s, 3H,
OCH3), 3.37 ,dd, J8.8, 9.2 Hz, 1H, CH2OMe), 3.43 ,dd,
J4.0, 9.2 Hz, 1H, CH2OMe), 4.09 ,dd, J4.0, 8.8 Hz, 1H,
PhCHCH2), 7.24±7.29 ,m, 1H, Ph), 7.31±7.39 ,m, 4H, Ph);
,d, J6.4 Hz, 3H, ,CH3)2CHN), 1.05 ,d, J6.4 Hz, 3H,
,CH3)2CHN), 1.14 ,d, J6.0 Hz, 3H, ,CH3)2CHO),
1.15 ,d, J6.0 Hz, 3H, ,CH3)2CHO), 2.76 ,m, 2H,
PhCH2CHCH), 2.93 ,sept., J6.4 Hz, 1H, ,CH3)2CHN),
2.99 ,m, 1H, PhCH2CHCH2), 3.27 ,m, 2H, PhCH2CHCH2),
3.52 ,sept., J6.0 Hz, 1H, ,CH3)2CHO), 7.17±7.23 ,m, 3H,
20
[a]D 175.4 ,c 2.3, ethanol); nmax ,liquid ®lm) 3328,
1110 cm21
C15H24NO requires 234.1858.
;
HRMS ,FAB): MH1, found 234.1886.
Ph), 7.27±7.32 ,m, 2H, Ph); [a]D 114.2 ,c 2.6, ethanol);
20
nmax ,liquid ®lm) 3323, 1173, 1128, 1080 cm21; HRMS
,FAB): MH1, found 236.2011. C15H26NO requires
236.2014.
4.7.9. /S)-N-Cyclohexyl-O-ethylphenylglycinol /2h).
Colorless oil ,90%); 1H NMR ,400 MHz, CDCl3) d
1.00±1.18 ,m, 5H, ,CH2)5CHN), 1.20 ,t, J7.0 Hz, 3H,
CH3CH2O), 1.54 ,m, 1H, ,CH2)5CHN), 1.63±1.74 ,m, 3H,
,CH2)5CHN), 2.02 ,m, 1H, ,CH2)5CHN), 2.29 ,m, 1H,
,CH2)5CHN), 3.77 ,t, J9.2 Hz, 1H, PhCHCH2), 3.46±
3.56 ,m, 3H, PhCHCH2 and CH3CH2O), 4.09 ,dd, J4.0,
9.2 Hz, 1H, PhCHCH2), 7.25±7.28 ,m, 1H, Ph), 7.30±7.35
4.7.15. /S)-N-Isopropyl-O-methylvalinol /4a). Colorless
oil ,60%); spectral data consistent with literature.20,22,23
4.7.16. /S)-N-Isopropyl-O-ethylvalinol /4b). Colorless oil
1
,60%); H NMR ,400 MHz, CDCl3) d 0.92 ,d, J7.2 Hz,
6H, ,CH3)2CHC), 1.05 ,d, J6.2 Hz, 3H, ,CH3)2CHN), 1.05
,d, J6.2 Hz, 3H, ,CH3)2CHN), 1.19 ,t, J6.8 Hz, 3H,
CH3CH2O), 1.85 ,m, 1H, ,CH3)2CHC), 2.55 ,q, J5.6 Hz,
1H, i-PrCHCH2), 2.86 ,sept., J6.2 Hz, 1H, ,CH3)2CHN),
3.22 ,dd, J5.6, 9.4 Hz, 1H, i-PrCHCH2), 3.41 ,dd, J5.6,
9.4 Hz, 1H, i-PrCHCH2), 3.48 ,q, J6.8 Hz, 2H,
20
,m, 2H, Ph), 7.36±7.40 ,m, 2H, Ph); [a]D 170.1 ,c 2.3,
ethanol); nmax ,liquid ®lm) 3326, 1110 cm21; HRMS
,FAB): MH1, found 248.2016. C16H26NO requires
248.2014.
20
4.7.10. /R)-N-/2-Methoxybenzyl)-O-methylphenylglycinol
/2i). Colorless oil ,40%); H NMR ,400 MHz, CDCl3) d
CH3CH2O); [a]D 23.6 ,c 2.9, ethanol); nmax ,liquid
1
®lm) 3327, 1173, 1119 cm21; HRMS ,FAB): MH1, found
3.31 ,s, 3H, CH3OCH2), 3.41±3.45 ,m, 2H, PhCHCH2),
3.55 ,d, J13.4 Hz, 1H, ArCH2N), 3.74 ,d, J13.4 Hz,
1H, ArCH2N), 3.83 ,s, 3H, CH3OAr), 3.92 ,dd, J5.4,
7.8 Hz, 1H, PhCHCH2), 6.83±6.94 ,m, 2H, Ar), 7.13±7.16
174.1889. C10H24NO requires 174.1858.
4.7.17. /S)-N-Isopropyl-O-isopropylvalinol /4c). Color-
less oil ,25%); H NMR ,400 MHz, CDCl3) d 0.90 ,d,
1
,m, 1H, Ar), 7.20±7.25 ,m, 1H, Ar), 7.25±7.31 ,m, 1H, Ph),
J6.4 Hz, 6H, ,CH3)2CHCH), 1.04 ,m, 6H, ,CH3)2CHN),
1.14 ,d, J6.0 Hz, 6H, ,CH3)2CHO), 1.83 ,m, 1H,
,CH3)2CHCH), 2.50 ,m, 1H, i-PrCHCH2), 2.84 ,sept.,
J6.4 Hz, 1H, ,CH3)2CHN), 3.29 ,m, 1H, i-PrCHCH2),
3.39 ,m, 1H, i-PrCHCH2), 3.52 ,sept., J6.0 Hz, 1H,
®lm) 3330, 1174, 1127, 1085 cm21; HRMS ,FAB): MH1,
found 188.1999. C11H26NO requires 188.2014.
20
7.33±7.39 ,m, 2H, Ph), 7.40±7.44 ,m, 2H, Ph); [a]D
171.6 ,c 2.7, ethanol); nmax ,liquid ®lm) 3336, 1240,
1128, 1100, 1026 cm21; HRMS ,FAB): MH1, found
272.1660. C17H22NO2 requires 272.1651.
20
,CH3)2CHO); [a]D 25.0 ,c 1.9, ethanol); nmax ,liquid
4.7.11. /R)-N-/2-Methoxybenzyl)-ethylphenylglycinol /2j).
Colorless oil ,80%); 1H NMR ,400 MHz, CDCl3) d 1.18 ,t,
J7.0 Hz, 3H, CH3CH2O), 3.40±3.50 ,m, 4H, CH3CH2O
and PhCHCH2), 3.56 ,d, J13.6 Hz, 1H, ArCH2N), 3.74
,d, J13.6 Hz, 1H, ArCH2N), 3.84 ,s, 3H, CH3O), 3.91
,dd, J4.0, 9.6 Hz, 1H, PhCHCH2), 6.85±6.92 ,m, 2H,
Ar), 7.13±7.16 ,m, 1H, Ar), 7.21±7.26 ,m, 1H, Ar),
7.28±7.31 ,m, 1H, Ph), 7.33±7.38 ,m, 2H, Ph), 7.41±7.45
4.7.18. /S)-N-/2-Methoxybenzyl)-O-methylvalinol /4d).
Colorless oil ,30%); H NMR ,400 MHz, CDCl3) d 0.92
1
,t, J6.8 Hz, 6H, ,CH3)2CHC), 1.92 ,m, 1H, ,CH3)2CHC),
2.55 ,m, 1H, i-PrCHCH2), 3.85 ,s, 3H, CH3O), 3.41±3.44
,m, 2H, i-PrCHCH2), 3.82 ,m, 2H, ArCH2N), 3.32 ,s, 3H,
CH3OAr), 6.85±6.95 ,m, 2H, Ar), 7.22±7.30 ,m, 2H, Ar);
20
,m, 2H, Ph); [aD 176.4 ,c 3.2, ethanol); nmax ,liquid
20
®lm) 3345, 1241, 1108 cm21; HRMS ,FAB): MH1, found
286.1794. C18H24NO2 requires 286.1807.
[a]D 210.2 ,c 2.2, ethanol); nmax ,liquid ®lm) 3337,
1240, 1113, 1049, 1030 cm21; HRMS ,FAB): MH1,
found 238.1854. C14H24NO2 requires 238.1807.
4.7.12. /S)-N-Isopropyl-O-methylphenylalaninol /3a).
Colorless oil ,80%); spectral data consistent with
literature.20,22,23
4.7.19. /S)-N-/2-Methoxybenzyl)-O-ethylvalinol /4e).
Colorless oil ,60%); H NMR ,400 MHz, CDCl3) d 0.92
1
,t, J7.6 Hz, 6H, ,CH3)2CHCH), 1.19 ,t, J7.0 Hz, 3H,
CH3CH2O), 1.93 ,m, 1H, ,CH3)2CHCH), 2.56 ,m, 1H,
i-PrCHCH2), 3.38 ,m, 1H, i-PrCHCH2), 3.42±3.50 ,m,
3H, i-PrCHCH2 and CH3CH2O), 3.83 ,s. 2H, ArCH2N),
4.7.13. /S)-N-Isopropyl-O-ethylphenylalaninol /3b).
Colorless oil ,50%); H NMR ,400 MHz, CDCl3) d 1.07
,d, J6.4 Hz, 3H, ,CH3)2CHN), 1.12 ,d, J6.4 Hz, 3H,
1