Enantioselective Synthesis of cis-3-Fluoropiperidin-4-ol, a Building Block for Medicinal Chemistry
Simon J. Shaw; Dane A. Goff; Luke A. Boralsky; Mark Irving; Rajinder Singh; Journal of Organic Chemistry 78 (2013) 8892–8897; doi:10.1021/jo401352z

data_4028549
_publ_contact_author_name
;
;
_publ_section_title
;
 Enantioselective Synthesis of cis-3-Fluoropiperidin-4-ol, a Building
 Block for Medicinal Chemistry
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              8892
_journal_page_last               8897
_journal_paper_doi               10.1021/jo401352z
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H18 F N O3'
_chemical_formula_sum            'C10 H18 F N O3'
_chemical_formula_weight         219.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_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_date             2011-10-11
_audit_creation_method
;
  Olex2 1.1
  (compiled Aug 18 2011 06:34:35, GUI svn.r3819)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 97.9620(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   7.76740(10)
_cell_length_b                   8.73290(10)
_cell_length_c                   8.48740(10)
_cell_measurement_reflns_used    3181
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.06
_cell_measurement_theta_min      5.06
_cell_volume                     570.167(12)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
XS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3472
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         70.05
_diffrn_reflns_theta_min         5.26
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_max  0.9731
_exptl_absorpt_correction_T_min  0.8385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
"SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.0610 before and 0.0333 after correction.
The Ratio of minimum to maximum transmission is 0.8617.
The \l/2 correction factor is 0.00.
{Info from C:\structures\rigel\x1110004\x1110004.abs}
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       plate
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.114
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.16(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         1994
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0300
_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^)+(0.0517P)^2^+0.0830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0804
_refine_ls_wR_factor_ref         0.0809
_reflns_number_gt                1954
_reflns_number_total             1994
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401352z_si_002.cif
_cod_data_source_block           x1110004
_cod_database_code               4028549