Trifluoroacetic acid → (4s,5r,6s)-6-Amino-7-cyclohexyl-4,5-dihydroxy-1-heptyne

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Reaction Steps

To a solution of the diol heptyne of Step 6 isomer (2.85 mmol) in CH2Cl2 (5.5 mL) was added trifluoroacetic acid (71.3 mmol). The reaction was monitored by TLC (50% EtOAc in hexane). After 30 minutes the solution was concentrated and an aqueous 1.0N NaOH solution (7 mL) was added. The solution was extracted with EtOAc (4×10 mL). The organic layer was dried with MgSO4. The filtrate was concentrated to give the title amine as a white sticky solid (0.67 g, 100% yield). The 1H, 13C and APT NMR spectral data were consistent with the prepared structure.

Provenance & Evidence