Triethylamine → 1-Benzyl-1,2,3,4-tetrahydroquinolin-7-yl 2-fluorophenylcarbamate

A mixture of 1-benzyl-1,2,3,4-tetrahydroquinolin-7-ol (805 mg, 3.36 mM) and triethylamine (0.6 mL) in dry tetrahydrofuran (THF, 5 ml) was stirred for half an hour under nitrogen atmosphere at room temperature (35° C.). To the stirred reaction mixture, 2-fluorophenyl isocyanate (565 mg/ml, 5.04 mM) was added at once and then the reaction mixture was further stirred for 72 hours under N2 atmosphere at RT. The reaction mixture was concentrated under vacuum and then was added distilled water (15 mL) followed by the extraction with ether (3×15 mL). The ether layer was dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was finally chromatographed using chloroform-hexane (1:9) to give 8c as oil. Yield: 1.02 g, 80.56%.

1. additionwas added at once and then the reaction mixture
2. stirringwas further stirred for 72 hours under N2 atmosphere at RT
3. concentrationThe reaction mixture was concentrated under vacuum
4. additionwas added
5. distillationdistilled water (15 mL)
6. extractionfollowed by the extraction with ether (3×15 mL)
7. dry with materialThe ether layer was dried over sodium sulphate
8. concentrationconcentrated under vacuum
9. customto afford the crude product, which
10. customwas finally chromatographed

ORD record

ord-67b555340d0f4b5e8e3b126b1eee5e6a

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08946261B2