反応 #69713

反応方程式

4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole

2,4-bis-benzyloxy-5-isopropenyl-benzoic acid

diisopropylethylamine

bromo-tris-pyrrolidino-phosphonium hexafluorophosphate

→

(2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone

溶媒

DCM

DCM

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   洗浄washed with water, 1N sodium hydroxide solution and brine
3. 3
   乾燥The organic phase was dried (MgSO4)
4. 4
   濃縮concentrated
5. 5
   その他to give a residue which
6. 6
   その他was absorbed onto an SCX column
7. 7
   洗浄This was washed with 10% methanol/DCM
8. 8
   洗浄the product was eluted with 25% 2M methanolic ammonia/DCM)

実験手順

A solution of 2,4-bis-benzyloxy-5-isopropenyl-benzoic acid (210 mg, 0.56 mmol) and diisopropylethylamine (0.25 mL, 1.4 mmol) in DCM (5 mL) was treated with bromo-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBrOP) (287 mg, 0.62 mmol). After 1 hour a solution of 4-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-isoindole (0.56 mmol, assuming a quantitative yield from the preceding step (C18)) in DCM (5 mL) was added. After 4 hours the mixture was diluted with ethyl acetate and washed with water, 1N sodium hydroxide solution and brine. The organic phase was dried (MgSO4) and concentrated to give a residue which was absorbed onto an SCX column. This was washed with 10% methanol/DCM then the product was eluted with 25% 2M methanolic ammonia/DCM) to afford an impure sample of the intermediate (2,4-bis-benzyloxy-5-isopropenyl-phenyl)-[4-(3-morpholin-4-yl-propoxy)-1,3-dihydro-isoindol-2-yl]-methanone.

出典