Reaktion #49408

ord-13d52efe4ce0416483a44112eb54336f

Reaktionsgleichung

CC(C)(C)OC(=O)n1c(-c2ccc(O)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21
4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone
CCN(CC)CC
triethylamine
O=S(=O)(Cl)c1ccccc1
benzenesulfonyl chloride
CC(C)(C)OC(=O)n1c(-c2ccc(OS(=O)(=O)c3ccccc3)c3c2C(=O)NC3)cc2cc(CN3CCCCC3)ccc21
4-benzenesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone
Ausbeute 86.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigefollowed by purification by flash column chromatography (chloroform/methanol=85/15)

Vorschrift

In a similar manner to Step 1 of Example 227, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.171 g, 0.371 mmol) was dissolved in dichloromethane (3.5 mL), and the solution was treated with triethylamine (0.103 mL, 0.741 mmol) and benzenesulfonyl chloride (0.0570 mL, 0.446 mmol), followed by purification by flash column chromatography (chloroform/methanol=85/15) to obtain 4-benzenesulfonyloxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.192 g. yield 86%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745641B2uspto-grants-2010_06