Abstract
An enantiomerically pure, conformationally constrained β-proline
derivative, 3,4-methano-β-proline, was synthesized starting
with a readily available bicyclic lactone by using a straightforward
synthetic route.
Key words
3,4-methano-β-proline - conformationally constrained β-amino
acid - enantioselective synthesis
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18
HPLC Data for
Boc-(3
R
,4
R
)-Methano-β-proline
Methyl Ester
t
R = 13.622
(min), area = 100%; OJ-H, IPA-n -hexane = 5:95; flow
rate = 0.4 mL/min, 25 ˚C, λ = 220
nm.
19
Crystal Data for
Compound 1
11 H17 NO4 ,
crystal size: 0.10 × 0.20 × 0.20
mm³ , M
r = 227.26
g mol-¹ , monoclinic, space group P 21, λ = 0.71073 Å, a = 6.1437
(8) Å, b = 11.3449
(17) Å, c = 9.3146
(13) Å, α = 90, β = 104.369
(10),
γ
= 90, V = 628. 92
(15) ų , Z = 2,
ρ
calcd = 1.200
g cm-³ ,
µ
= 0.091 min-¹ , T = 293 (2)
K,
θ
range = 3.6-33.2˚;
reflections collected: 10063, independent: 4247 (R
int = 0.037).
The structure was solved by direct methods and refined by full-matrix
least-squares on F² ; R
1 = 0.0432, wR
2 = 0.1196 [ I > 2σ (I)];
maximal residual electron density: 0.12 e Å-³ . CCDC
710057 contains the supplementary crystallographic data for this
structure. These data can be obtained free of charge from the Cambridge
Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
20 Flack HD.
Acta
Crystallogr., Sect. A: Fundam. Crystallogr.
1983,
39:
876 ; the Flack parameter of the crystal structure
of 1 was 0.0(10), and that of ent -1 was 1.0(10)
21
HPLC Data for
Boc-(3
R
)-β-proline
Methyl Ester
t
R = 20.621
(min), area = 100%; racemic
Boc-β-proline methyl ester, t
R = 15.985,
20.824 (min). OJ-H, IPA-n -hexane = 5:95;
flow rate = 0.4 mL/min, 25 ˚C, λ = 220
nm.
