HCID 59680788, compound → HCID 10840267, compound

Participants

Reaction Conditions

Reaction Steps

To a homogeneous solution of D2 (24.49 g, 38.4 mmol) in aq AcOH (211 ml, 90%) at 0° C., powdered Zn was added (18.65 g, 288.3 mmol). The resulting mixture was stirred at 0° C. for 3 h until disappearance of the staffing material (followed by TLC). The reaction mixture was filtered over celite and washing with EtOAc (200 ml). The filtrate was concentrated at reduced pressure and the residue was chased with Et2O (200 ml) and filtered. The filtrate was successively partitioned between aq KHSO4 (100 ml, 10%) and brine (100 ml). The organic phase was dried (Na2SO4) and concentrated to give an oil which was purified by flash LC (Lichroprep RPC18, ACN:H2O 1:1 (800 ml, then 7:3 (600 ml)] to yield D1 (15.53 g, 74%) as a white solid. [α]D24 −27.6 (c 2.187, DCM); lit [α]D −20.5 (c 2, DCM). JOC, 62, 2, 1997. Rf=0.58 [ACN/H2O (7:3)].

Provenance & Evidence