Table 1. Reaction Condition Optimization of the Deacetylation of Compound 11a.
entry | reagents | solvent | T (°C) | 12 (% yield)b (%) | 12a (% yield)b (%) |
---|---|---|---|---|---|
1 | K2CO3c | MeOH/DCM | r.t. to 40 °Cd | 0 | 0 |
2 | 10% LiOH | MeOH/DCM | r.t. to 40 °Cd | 30 | 25 |
3 | 10% NaOH | MeOH/DCM | r.t. to 40 °Cd | 51 | 19 |
4 | 10% KOH | MeOH/DCM | r.t. to 40 °Cd | 47 | 23 |
5 | LiAlH4 | THF | 0 °C to r.t. | 81 | 0 |
Reaction conditions: 11 (0.1 mmol), reagents (1.0 mmol, 10.0 equiv), solvent (3.0 mL, MeOH/DCM, v/v = 2:1), 16 h.
Isolate yield.
Saturated aqueous.
Stirred at room temperature for 10 h (no reaction), then rise to 40 °C and stirred for another 6 h.