Aniline → HCID 57663775, compound

To a stirred solution of tert-butyl 4-oxo-2a-(2-oxoethyl)-2a,3,4,5-tetrahydropyrrolo[4,3,2-de]quinolin-1(2H)-carboxylate, enantiomer A, (150 mg, 0.474 mmol, described in Intermediate 24) in CH2Cl2 (2 mL) at 0° C. was added DAST (0.125 mL, 0.948 mmol) and the mixture was stirred for 1 h. Additional DAST (0.066 mL) was added and the mixture was stirred for 1 h. To the resulting mixture was added TFA (2 mL) and stirring was continued for 1 h. The mixture was concentrated in vacuo and partitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (10 mL). The layers were separated and the aqueous layer further extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 95:5, to give the title compound. MS: m/z=239 (M+1).

1. stirringthe mixture was stirred for 1 h
2. stirringstirring
3. waitwas continued for 1 h
4. concentrationThe mixture was concentrated in vacuo
5. custompartitioned between saturated aqueous NaHCO3 (10 mL) and CH2Cl2 (10 mL)
6. customThe layers were separated
7. extractionthe aqueous layer further extracted with CH2Cl2 (2×10 mL)
8. dry with materialThe combined organic layers were dried over Na2SO4
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customThe crude product was purified by silica gel chromatography
12. washeluting with a gradient of CH2Cl2

ORD record

ord-7b39551c84ac4f6a8c3d7ab3ebf042f6

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07947677B2