Biomass derived furfural-based facile synthesis of protected (2S)-phenyl-3-piperidone, a common intermediate for many drugs
P.-F. Koh; P. Wang; J.-M. Huang; T.-P. Loh; Chem.Commun. 50 (2014) 8324–; doi:10.1039/C4cc02645D

data_7115326
_publ_section_title
;
 Biomass derived furfural-based facile synthesis of protected
 (2S)-phenyl-3-piperidone, a common intermediate for many drugs
;
_journal_name_full               Chem.Commun.
_journal_page_first              8324
_journal_paper_doi               10.1039/C4cc02645D
_journal_volume                  50
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_sum            'C21 H23 N O3 S'
_chemical_formula_weight         369.46
_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                 114.811(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.789(3)
_cell_length_b                   9.327(3)
_cell_length_c                   11.044(3)
_cell_measurement_reflns_used    595
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      20.82
_cell_measurement_theta_min      2.98
_cell_volume                     915.3(5)
_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      103(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0810
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3585
_diffrn_reflns_theta_full        26.89
_diffrn_reflns_theta_max         26.89
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.198
_exptl_absorpt_correction_T_max  0.9805
_exptl_absorpt_correction_T_min  0.9431
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.148
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.20(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3585
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0583
_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^)+(0.0926P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1394
_refine_ls_wR_factor_ref         0.1581
_reflns_number_gt                2960
_reflns_number_total             3585
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc02645d2.cif
_cod_data_source_block           ltp254_0m
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               7115326