Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and Stereochemical Assignment of (+)- and (-)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
Alexey Yu. Sukhorukov; Yaroslav D. Boyko; Sema L. Ioffe; Yulia A. Khomutova; Yulia V. Nelyubina; Vladimir A. Tartakovsky; Journal of Organic Chemistry 76 (2011) 7893–7900; doi:10.1021/jo201331h

data_4026617
_publ_section_title
;
 Synthesis of PDE IVb Inhibitors. 1. Asymmetric Synthesis and
 Stereochemical Assignment of (+)- and
 (-)-7-[3-(Cyclopentyloxy)-4-methoxyphenyl]hexahydro-3H-pyrrolizin-3-one
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7893
_journal_page_last               7900
_journal_paper_doi               10.1021/jo201331h
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C30 H30 N O8'
_chemical_formula_weight         532.55
_chemical_name_systematic
;

 ?

;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                63.6620(10)
_cell_angle_beta                 64.3830(10)
_cell_angle_gamma                67.5390(10)
_cell_formula_units_Z            2
_cell_length_a                   12.2643(10)
_cell_length_b                   12.6227(10)
_cell_length_c                   12.7582(11)
_cell_measurement_temperature    100(2)
_cell_volume                     1551.2(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18474
_diffrn_reflns_theta_full        29.00
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9796
_exptl_absorpt_correction_T_min  0.9715
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             562
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.915
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         8216
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0542
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1655
_refine_ls_wR_factor_ref         0.1761
_reflns_number_gt                6224
_reflns_number_total             8216
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201331h_si_002.cif
_cod_data_source_block           a
_cod_database_code               4026617