Sodium Iodide → HCID 68283670, compound

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C@H:13]([C:14]([OH:16])=[O:15])[CH2:12][C@:11]2([CH2:17]OS(C)(=O)=O)[C@H:9]1[CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Na+].[I-].CO[CH2:27][CH2:28]OC>[Zn]>[CH2:27]([O:16][C:14]([C@@H:13]1[CH2:12][C@:11]2([CH3:17])[C@@H:9]([CH2:10]2)[N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[O:15])[CH3:28]

Participants

Procedure

To a solution of (1R,3S,5S)-5-methanesulfonyloxymethyl-2-aza-bicyclo[3.1.0]hexane-2,3-dicarboxylic acid 2-tert-butyl ester (100 mg, 0.24 mmol) in DME (2.6 mL) were successively added NaI (355 mg, 2.37 mmol) and zinc powder (155 mg, 2.37 mmol). The reaction mixture was refluxed 30 min under argon atmosphere, cooled to RT and quenched by addition of a saturated aqueous solution of NH4Cl (1.6 mL). CH2Cl2 (1.6 mL) and few Na2S crystals were added and the biphasic mixture was stirred at RT for 1 h. The layers were separated, the organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude residue was purified by flash column chromatography on silica gel (eluent: c-hexane to c-hexane/EtOAc). TLC, Rf (c-hexane/EtOAc 2:1)=0.60; MS (UPLC/MS): 270.3 [M+H]+, 214.2 [MH−tBu]+, 170.2 [MH−Boc]+; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 4.11 (m, 2H), 3.95 (m, 1H), 3.10 (m, 1H), 2.42 (m, 1H), 1.84 (m, 1H), 1.38 (m, 9H), 1.20 (t, 3H), 1.18 (s, 3H) 0.69 (dd, 1H), 0.64 (m, 1H).