Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic Resolution
Hyeon-Kyu Lee; Soyeong Kang; Eun Bok Choi; Journal of Organic Chemistry 77 (2012) 5454–5460; doi:10.1021/jo300867y

data_4027251
_publ_section_title
;
 Stereoselective Synthesis of Norephedrine and Norpseudoephedrine by Using
 Asymmetric Transfer Hydrogenation Accompanied by Dynamic Kinetic
 Resolution
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5454
_journal_page_last               5460
_journal_paper_doi               10.1021/jo300867y
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C9 H11 N O3 S'
_chemical_formula_weight         213.25
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.753(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.6397(1)
_cell_length_b                   9.9763(2)
_cell_length_c                   7.5180(2)
_cell_measurement_reflns_used    3305
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.50
_cell_measurement_theta_min      2.71
_cell_volume                     497.415(18)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(1)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_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  0.0172
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4518
_diffrn_reflns_theta_full        28.57
_diffrn_reflns_theta_max         28.57
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.305
_exptl_absorpt_correction_T_max  0.9760
_exptl_absorpt_correction_T_min  0.9359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            silver
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             224
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.451
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.07(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         2000
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0289
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.1424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0770
_reflns_number_gt                1906
_reflns_number_total             2000
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo300867y_si_001.cif
_cod_data_source_block           20120117lt2_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4027251