Trifluoroacetic acid → ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate

To a solution of ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (4.5 g, 13.6 mmol) in CH2Cl2 (40 mL) at 0° C. was added TFA (20 mL) followed by NaCNBH3 (1.8 g, 27 mmol) and stirred at rt for 3 hours before the solvent was removed by the nitrogen stream. To the resulting residue were added CH2Cl2 (40 mL) and 6N HCl (20 mL) and stirred for 0.5 hour. The solution was diluted with water (20 mL), 1N NaOH (30 mL) and extracted with CH2Cl2 (2×30 mL). The combined extracts were dried over magnesium sulfate, concentrated, and purified by flash chromatography to afford ethyl 6-[(ethoxycarbonyl)amino]-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indole-2-carboxylate (3.6 g, 80%) as a clear oil. MS [M+H]+ 334. 1H NMR (CDCl3, 300 MHz): δ 6.97 (d, 1H, J=7.3 Hz), 6.85 (d, 1H, J=7.3 Hz), 6.72 (t, 1H, J=7.3 Hz), 4.05 (m, 4H), 3.41 (m, 4H), 1.92 (m, 2H), 1.20–1.24 (m, 6H) ppm.

1. customwas removed by the nitrogen stream
2. additionTo the resulting residue were added CH2Cl2 (40 mL) and 6N HCl (20 mL)
3. stirringstirred for 0.5 hour
4. additionThe solution was diluted with water (20 mL), 1N NaOH (30 mL)
5. extractionextracted with CH2Cl2 (2×30 mL)
6. dry with materialThe combined extracts were dried over magnesium sulfate
7. concentrationconcentrated
8. custompurified by flash chromatography

ORDレコード

ord-11974bb07b6a491abd50f9b6d9c3bb4c

出典データセット

uspto-grants-2007_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07183282B2