Synthesis of rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol. An unusual double rearrangement leading to the ortho- and para-f oxide-bridged phenylmorphan isomers.
Kodato, Shinichi; Linders, Joannes T. M.; Gu, Xiao-Hui; Yamada, Koichiro; Flippen-Anderson, Judith L; Deschamps, Jeffrey R.; Jacobson, Arthur E.; Rice, Kenner C.; Organic & biomolecular chemistry 2 (2004) 330–336; doi:10.1039/b312633c

data_7151596
_publ_section_title
;
 Synthesis of
 rac-(1R,4aR,9aR)-2-methyl-1,3,4,9a-tetrahydro-2H-1,4a-propanobenzofuro[2,3-c]pyridin-6-ol.
 An unusual double rearrangement leading to the ortho- and para-f
 oxide-bridged phenylmorphan isomers.
;
_journal_issue                   3
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              330
_journal_page_last               336
_journal_paper_doi               10.1039/b312633c
_journal_volume                  2
_journal_year                    2004
_chemical_formula_moiety         'C15 H20 N O2, Br'
_chemical_formula_sum            'C15 H20 Br N O2'
_chemical_formula_weight         326.23
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.14(2)
_cell_angle_beta                 97.91(2)
_cell_angle_gamma                103.65(2)
_cell_formula_units_Z            4
_cell_length_a                   10.841(2)
_cell_length_b                   11.998(3)
_cell_length_c                   12.157(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_volume                     1465.5(6)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_publication_material  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_refinement  'Bruker Shelxtl v6.10 (Bruker, 2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0835
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5233
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.803
_exptl_absorpt_correction_T_max  0.870
_exptl_absorpt_correction_T_min  0.616
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   'Bruker XPREP v5.1 (Bruker, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.828
_refine_diff_density_min         -0.497
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         4895
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.0754
_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^)+(0.0595P)^2^+9.1372P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1702
_refine_ls_wR_factor_ref         0.2017
_reflns_number_gt                2908
_reflns_number_total             4895
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            b312633c.txt
_cod_data_source_block           rice44
_cod_database_code               7151596