Stereoselective Synthesis of (S)-3-(Methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile
Manjinder S. Lall; Garrett Hoge; Tuan P. Tran; William Kissel; Sean T. Murphy; Clarke Taylor; Kim Hutchings; Brian Samas; Edmund L. Ellsworth; Timothy Curran; H. D. Hollis Showalter; Journal of Organic Chemistry 77 (2012) 4732–4739; doi:10.1021/jo3004716

data_4027201
_publ_section_title
;
 Stereoselective Synthesis of
 (S)-3-(Methylamino)-3-((R)-pyrrolidin-3-yl)propanenitrile
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              4732
_journal_page_last               4739
_journal_paper_doi               10.1021/jo3004716
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 118.686(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1291(16)
_cell_length_b                   7.6863(7)
_cell_length_c                   16.5264(16)
_cell_measurement_reflns_used    2082
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      19.88
_cell_measurement_theta_min      2.45
_cell_volume                     1797.4(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.951
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0382
_diffrn_reflns_av_sigmaI/netI    0.0400
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15579
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.45
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9928
_exptl_absorpt_correction_T_min  0.9739
_exptl_absorpt_correction_type   empirical
_exptl_crystal_density_diffrn    1.202
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.140
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         4236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0605
_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^)+(0.0555P)^2^+0.2646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                2609
_reflns_number_total             4236
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo3004716_si_002.cif
_cod_data_source_block           sad1
_cod_database_code               4027201