Diastereoselective Syntheses of (3R*,4R*)- and (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues
Sébastien Schmitt; Richard C. D. Brown; Cécile Perrio; Journal of Organic Chemistry 78 (2013) 1222–1229; doi:10.1021/jo302303h

data_4027890
_publ_section_title
;
 Diastereoselective Syntheses of (3R*,4R*)- and
 (3R*,4S*)-4-Aryl-3-methyl-4-piperidinemethanol and Fluoro Analogues
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1222
_journal_page_last               1229
_journal_paper_doi               10.1021/jo302303h
_journal_volume                  78
_journal_year                    2013
_chemical_compound_source        'Schmitt Sebastien'
_chemical_formula_sum            'C21 H30 N2 O3'
_chemical_formula_weight         358.47
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 112.905(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.523(4)
_cell_length_b                   20.652(6)
_cell_length_c                   9.308(3)
_cell_measurement_reflns_used    4757
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.2
_cell_measurement_theta_min      2.8
_cell_volume                     2040.4(11)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_molecular_graphics
;
Images generated using CrystalMaker: a crystal and molecular 
structures program for Mac and Windows. CrystalMaker Software Ltd, 
Oxford, England (www.crystalmaker.com)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'four-circle \k diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC12 (Right)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMesh'
_diffrn_radiation_collimation    'Confocal mirrors, HF Varimax '
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.1381
_diffrn_reflns_av_sigmaI/netI    0.1705
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            11525
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         3.09
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9992
_exptl_absorpt_correction_T_min  0.9961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Jacobson, R. (1998). REQAB. Private communication to the 
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_description       Plate
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3589
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.171
_refine_ls_R_factor_all          0.1862
_refine_ls_R_factor_gt           0.1226
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+1.0429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1956
_refine_ls_wR_factor_ref         0.2219
_reflns_number_gt                2245
_reflns_number_total             3589
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo302303h_si_001.cif
_cod_data_source_block           2012sot0041
_cod_original_cell_volume        2040.4(10)
_cod_database_code               4027890