3-Pentanamine → Tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4'-piperidine]-1'-carboxylate

A solution of 1-ethylpropylamine (0.5 mL) was added to a stirred solution of compound (C4) (0.50 g, 1.52 mmol), EDAC.HCl (0.6 g, 3.00 mmol), HOBt (0.31 g, 2.32 mmol) in DMF (10 mL) and the solution was stirred at room temperature for 2 h. The solution was poured into water (50 mL) and the aqueous layer was extracted with EtOAc (3×50 mL), dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by Biotage SP1 on silica gel eluting with 5-70% EtOAc in hexanes to provide tert-butyl 3-(pentan-3-ylcarbamoyl)spiro[inden-1,4′-piperidine]-1′-carboxylate (F1) as a white solid (0.6 g). LC/MS (10-90% over 3 min with 0.9% FA) m/z 399 (M+1), Rt 3.66 minutes. 1HNMR (500 MHz, DMSO-d6) δ 7.78 (d, 1H), 7.55 (m, 1H), 7.43 (d, 1H), 7.23 (br m, 1H), 4.07 (m, 2H), 3.75 (m,1H), 3.15 (m, 2H), 1.98 (d, 2H), 1.55 (m, 2H), 1.45 (s, 9H), 1.25 (m,2H), 0.88 (m, 6H).

1. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
2. dry with materialdried over Na2SO4
3. concentrationconcentrated under reduced pressure
4. customThe crude product was purified by Biotage SP1 on silica gel eluting with 5-70% EtOAc in hexanes

ORDレコード

ord-6e3893529d6245af9395725a23bdd9b2

出典データセット

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07858790B2