3580
N. W. Boaz et al. / Tetrahedron: Asymmetry 14 (2003) 3575–3580
calcd for C13H18NO2 (M+H)+: 220.1338, found:
220.1361. [h]2D4 +5.6 (c 1.0, CH3OH).
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4.8. Preparation of S-2-amino-3-cyclopropylpropionic
acid 7
Benzyl ester 6 (1.00 g; 4.6 mmol) was dissolved in 10
mL of methanol in a Parr bottle and 5% palladium on
carbon (50 mg; 5 wt%) was added. The reaction mix-
ture was shaken under 40 psig hydrogen at 50°C for 3
h and then cooled to ambient temperature. The reac-
tion mixture was filtered through Celite, eluted with hot
methanol, and concentrated to afford 0.58 g (98%) of 7
as a white solid. The crude product was dissolved in 6
mL of refluxing water, diluted with 45 mL of ethanol,
and cooled to 4°C overnight to afford 491 mg (83%) of
1
7 as a glistening white solid. H NMR (NaOD in D2O)
l 3.20 (t, 1H, J=6.0 Hz); 1.50–1.38 (m, 1H), 1.35–1.29
(m, 1H); 0.58–0.54 (m, 1H), 0.32–0.30 (m, 2H), −0.02 to
−0.04 (m, 2H). 13C NMR (NaOD in D2O+DMSO-d6) l
184.9, 58.0, 40.9, 8.5, 5.2, 5.0. Anal. calcd for
C6H11NO2: C, 55.80; H, 8.58; N, 10.84. Found: C,
55.90; H, 8.51; N, 10.78. [h]2D4 −12.8 (c 0.50, H2O) [Lit.5d
[h]D −12.7 (c 0.50, H2O)], [h]2D4 +14.5 (c 0.51, H2O/2 M
NaOH) [Lit.5d [h]D +13.4 (c 0.50, H2O/2 M NaOH)].
Acknowledgements
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The authors thank Mr. W. Dell Nottingham and Mr.
Matthew Elliot for scale-up assistance, Mr. James D.
Little for high resolution mass spectral analyses, and
Ms. Ellen F. Yeary for combustion analyses.
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