Boron tribromide → N-(t-butoxycarbonyl)-(+/-)-1,3,4,10b-tetrahydro-9-hydroxy-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one

To a stirring solution of N-(t-butoxycarbonyl)-(±)-1,3,4,10b-tetrahydro-9-methoxy-7-trifluoromethoxy-pyrazino[2,1-a]isoindol-6(2H)-one (201 mg, 0.5 mmol) in dry CH2Cl2 (3 mL) at −78° C. under Ar was added IM boron tribromide in CH2Cl2 (1.75 mL). The reaction was stirred for 1 h and then warmed to room temperature for 18 h. The reaction was refluxed for 24 h and then quenched with water. The reaction was stirred for 30 min and then conc. in vacuo to a brown solid. The solid was treated with 6M HCl. After 1 h, the reaction was conc. in vacuo to a brown solid. The solid was partioned between water and EtOAc, basified with sodium bicarbonate, and treated with di-t-butyl dicarbonate (109 mg, 0.5 mmol). The reaction was stirred for 1 h and extracted with EtOAc (3×10 mL). The organic layers were combined, dried over MgSO4, and conc. in vacuo to a brown solid. The solid was purified by trituration with chloroform to yield 103 mg of the desired product as a white solid. MS (ESI) 389 (M+H).

1. temperatureThe reaction was refluxed for 24 h
2. customquenched with water
3. stirringThe reaction was stirred for 30 min
4. additionThe solid was treated with 6M HCl
5. waitAfter 1 h
6. stirringThe reaction was stirred for 1 h
7. extractionextracted with EtOAc (3×10 mL)
8. dry with materialdried over MgSO4
9. customThe solid was purified by trituration with chloroform

ORDレコード

ord-e15ddd24676f4eb2a68ccf0298f64247

出典データセット

uspto-grants-2010_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07812024B2