Hydrochloric Acid → HCID 15029887, compound

Participants

Reaction Steps

The product of Example 93 (2 g) was dissolved in anhydrous MeOH (20 ml) and EtNH2 (3 ml) and the pH adjusted to ca. 8 with methanolic HCl. Sodium cyanoborohydride (500 mg) was added and an additional 2 ml methanolic HCl dropwise. The reaction was stirred under N2 for 48h then 6 N HCl added to pH<2. The methanol was removed under vacuum and the aqueous layer extracted with CH2Cl2 (2×100 ml). The organic layer was separated, washed with brine, dried (MgSO4), filtered and evaporated giving 0.18 g of an oil. The neutral CH2Cl2 extract was dried (MgSO4), filtered and evaporated then partitioned between 2 N HCl and a mixture of ether/hexane. The organic layer was separated and discarded. The acidic layer was basified and extracted with CH2Cl2. The organic layer was separated, dried (MgSO4), filtered and evaporated giving an additional 1.12 g of product.

Provenance & Evidence