Synthesis of All Four Stereoisomers of 3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid
Bettina Bakonyi; Markus Furegati; Christian Kramer; Luigi La Vecchia; Flavio Ossola; Journal of Organic Chemistry 78 (2013) 9328–9339; doi:10.1021/jo4013282

data_4028599
_publ_contact_author_address
;
      Novartis Institutes for BioMedical Research
      WKL-122.U1.28
      CH-4057 Basel
      Switzerland
;
_publ_contact_author_email       markus.furegati@novartis.com
_publ_contact_author_fax         0041-61-6964576
_publ_contact_author_name        'Markus Furegati'
_publ_contact_author_phone       0041-61-6968016
_publ_section_title
;
 Synthesis of All Four Stereoisomers of
 3-(tert-Butoxycarbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic Acid
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9328
_journal_page_last               9339
_journal_paper_doi               10.1021/jo4013282
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C11 H16 N O4 1-, C8 H12 N O 1+'
_chemical_formula_sum            'C19 H28 N2 O5'
_chemical_formula_weight         364.43
_chemical_name_systematic
; 
(R)-phenylglycinol salt of (+)-Trans-(1R,2R,5S)-3-(tert-butoxy-
carbonyl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid.
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.030(6)
_cell_length_b                   7.997(7)
_cell_length_c                   39.32(4)
_cell_measurement_reflns_used    9038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.50
_cell_volume                     1896(3)
_computing_cell_refinement       'SAINT V7.36A (Bruker AXS, 2006)'
_computing_data_collection       'SMART V5.632 (Bruker AXS, 2005)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2006)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device_type  "'three-circle goniometer"
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'MicroStar rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            38232
_diffrn_reflns_theta_full        68.51
_diffrn_reflns_theta_max         68.51
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.7124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_description       needle
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3418
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0318
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+0.5572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0805
_reflns_number_gt                3357
_reflns_number_total             3418
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4013282_si_002.cif
_cod_data_source_block           MFU10a
_cod_database_code               4028599