反应 #312604

反应方程式

Dioxide

3-(Benzyloxymethyl)-isothiazolidine 1,1-dioxide

→

hydroxyl-dioxide

收率 67.0%

3-(Hydroxymethyl)-isothiazolidine 1,1-dioxide

收率 67.0%

溶剂

—

IMS

iPrOAc

iPrOAc

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.WAITAfter a further 4 days the reaction was
3. 3
   过滤The palladium catalyst was filtered under nitrogen on a bed of celite, which
4. 4
   洗涤was subsequently washed with IMS (250 mL) and iPrOAc (250 mL)
5. 5
   浓缩The filtrate and washings were concentrated
6. 6
   其他to give the crude product as an oil (26.26 g)
7. 7
   其他The oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1))

实验过程

Dioxide 7 (40 g, 0.17 mol) was placed in the glass liner within a 2 L Parr hydrogenator and dissolved in a mixture of IMS (150 ml) and iPrOAc (150 ml). A suspension of 5% palladium on carbon (Johnson Matthey type 392, 18 g) in iPrOAc (50 mL) was added and the suspension stirred under a hydrogen atmosphere of 70 psi for 3 days. After this time an NMR IPC was carried out that showed approx 15% benzylated material still present. After a further 4 days the reaction was 94% complete and it was decided to stop the hydrogenolysis. The palladium catalyst was filtered under nitrogen on a bed of celite, which was subsequently washed with IMS (250 mL) and iPrOAc (250 mL). The filtrate and washings were concentrated to give the crude product as an oil (26.26 g). The oil was purified by flash column chromatography (silica gel, DCM/methanol (9:1)) yielding 16.65 g (67%) of the hydroxyl-dioxide 8 as a white solid.

来源