B.CSC.[CH2:5]([O:9][S:10]([CH:13]1[CH2:16][C:15](=[C:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH2:14]1)(=[O:12])=[O:11])[CH2:6][CH2:7][CH3:8].C(OCC)(=O)C>C1COCC1>[OH:19][CH2:18][CH:17]([CH:15]1[CH2:14][CH:13]([S:10]([O:9][CH2:5][CH2:6][CH2:7][CH3:8])(=[O:12])=[O:11])[CH2:16]1)[CH2:23][OH:24]Borane-DMS (0.2 mL, 2.3 mmol) was added to a solution of diethyl 2-(3-(butoxysulfonyl)cyclobutylidene)malonate (0.2 g, 0.575 mmol) in THF (5 mL) and the resulting reaction mass was stirred at room temperature overnight. The reaction was monitored by TLC (100% ethyl acetate). The reaction mixture was quenched with 1N HCl and extracted using ethyl acetate. The organic layer was washed with brine solution, dried over anhydrous Na2SO4 and concentrated. Purification by column chromatography on silica gel (70% ethyl acetate in hexane) afforded 0.13 g of the product (74% yield).
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