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  (Organic Chemistry)

Boc Deprotection



Example 1

To a solution of the SM (0.16 g, 0.39 mmol) in CHCl3 (3.0 mL) was added dropwise TMSI (93 mg, 0.46 mmol) at RT. The reaction mixture was stirred at RT overnight. The mixture was concentrated in vacuo and the resulting residue was dissolved in H2O (10 mL) and acidified with 1N HCl to pH ~3. The aq layer was extracted with EtOAc (3 x 30 mL). The aq layer was then basified with 5% aq Na2CO3 to pH ~9, and was extracted with 3:1 CHCl3/IPA (3 x 30 mL). The combined organics were washed with brine (3 x 30 mL), dried (Na2SO4), and concentrated to provide the product as a brown syrup. [100 mg, 83%]

[Patent Reference: WO2010016005, page 125, (11.3 MB)]