ChemicalBook CAS DataBase List N-BOC-1-[4-SPIRO-PIPERIDINE]-3-INDANONE

N-BOC-1-[4-SPIRO-PIPERIDINE]-3-INDANONE synthesis

8synthesis methods

Product Name:N-BOC-1-[4-SPIRO-PIPERIDINE]-3-INDANONE
CAS Number:159634-59-0
Molecular formula:C18H23NO3
Molecular Weight:301.38

137419-24-0
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$45.00/50mg

159634-59-0
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$60.00/25 mg

Yield: 78.7%

Reaction Conditions:

Stage #1:1'-(tert-butyloxycarbonyl)spiro<1H-indene-1,4'-piperidine> with 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran at 20; for 24 h;Inert atmosphere;
Stage #2: with pyridinium chlorochromate in dichloromethane at 0;Reflux;

Steps:

13.1
Under an argon atmosphere, a solution of t-butyl spiro(indene-1,4'-piperidine)-1'-carboxylate (514 mg, 1.80 mmol) in tetrahydrofuran (5 mL) was added with a solution of 9-borabicyclo[3.3.1]nonane in tetrahydrofuran (0.5 M, 10.5 mL) at room temperature, and the resultant was stirred at the same temperature for 24 hours. The reaction solution was concentrated in vacuo, dissolved into dichloromethane (8 mL), and added with pyridinium chlorochromate (2.30 g, 10.7 mmol) at 0° C. The resultant was stirred for 2 hours by heating under reflux. The reaction solution was filtered using celite, and concentrated in vacuo. The resultant residue was purified using silica-gel chromatography (hexane:ethylacetate=4:1), and t-butyl 3-oxo-2,3-dihydrospriro(indene-1,4'-piperidine-1'-carboxylate (23.5 mg, 78.7%) was obtained as a colorless oil.¹H-NMR (400 MHz, CDCl₃) δ; 1.46-1.57 (m, 2H), 1.50 (s, 9H), 1.96-2.01 (m, 2H), 2.64 (s, 2H), 2.80-2.89 (m, 2H), 4.20-4.26 (br, 2H), 7.42 (t, J=7.3 Hz, 1H), 7.49 (d, J=7.3 Hz, 1H), 7.65 (t, J=7.3 Hz, 1H), 7.74 (d, J=7.3 Hz, 1H).

References:

KOWA COMPANY, LTD. US2010/22572, 2010, A1 Location in patent:Page/Page column 17-18

185525-42-2 Synthesis