反応 #88931
ord-1100536bb7104000a14be99016408b0c
反応方程式
反応物
試薬
溶媒
反応条件
後処理
- 1温度The mixture was cooled to 0° C.
- 2workup.STIRRINGstirred at RT for 1 h
- 3温度The mixture was cooled to 0° C.
- 4その他quenched by dropwise addition of water
- 5その他to give a gel that
- 6その他was partitioned between EtOAc/ether and brine/water/aqueous potassium sodium tartrate solution
- 7ろ過The insoluble salts were filtered off
- 8その他the phases separated
- 9抽出The aqueous phase was extracted with EtOAc (2×)
- 10洗浄the combined organic layers were washed with a 10% aqueous citric acid solution, saturated sodium bicarbonate solution and brine
- 11乾燥dried (Na2SO4)
- 12ろ過filtered
- 13その他evaporated in vacuo
- 14その他purified by FCC
実験手順
A solution of Intermediate 61a (2.88 g, 6.60 mmol) in DCM (50 mL) at 0° C. under N2 was treated dropwise with diisobutyl aluminium hydride (1.0M in THF, 16.6 mL, 16.6 mmol) and the mixture was stirred at RT overnight. The mixture was cooled to 0° C., then treated dropwise with another portion of diisobutyl aluminium hydride (1.0M in THF, 8.3 mL, 8.30 mmol) and stirred at RT for 1 h. The mixture was cooled to 0° C. and quenched by dropwise addition of water to give a gel that was partitioned between EtOAc/ether and brine/water/aqueous potassium sodium tartrate solution. The insoluble salts were filtered off and the phases separated. The aqueous phase was extracted with EtOAc (2×) and the combined organic layers were washed with a 10% aqueous citric acid solution, saturated sodium bicarbonate solution and brine, dried (Na2SO4), filtered and evaporated in vacuo. The residue was pre-adsorbed onto diatomaceous earth and purified by FCC, using 0-15% EtOAc in cyclohexane, to give the title compound as a colorless oil (1.04 g, 39%). LCMS (Method 3): Rt 5.29 min, m/z 405 [MH+].