9-Borabicyclo(3.3.1)nonane → 1'-(t-butyloxycarbonyl)-3,4-dihydro-3-oxospiro[1H-indene-1,4'-piperidine]

Temperature

70 °C

To a solution of 661 mg (2.31 mmol) of 1'-(t-butyloxycarbonyl)spiro[1H-indene-1,4'-piperidine] [prepared by the method of Chambers, et al, J. Med. Chem., 1992, 35, 2036] in 5.0 ml of THF was added 5.8 ml (1.0M THF, 2.9 mmol) of 9-BBN. The reaction mixture was heated at 70° C. until TLC analysis indicated that the starting material was consumed. The solution was concentrated and the residue was dissolved in dichloromethane. The solution was cooled to 0° C. and 4.1 g (19.2 mmol) of PCC was added slowly over 15 minutes. The reaction mixture was warmed to room temperature and then to reflux for 30 minutes. The solution was then diluted with ether and filtered through a pad of a mixture of celite and florisil. Purification by flash chromotography (silica gel, hexane/ethyl acetate, 4:1) gave 326 mg (47%) of the title compound.

1. customwas consumed
2. concentrationThe solution was concentrated
3. dissolutionthe residue was dissolved in dichloromethane
4. temperatureThe solution was cooled to 0° C.
5. temperatureThe reaction mixture was warmed to room temperature
6. temperatureto reflux for 30 minutes
7. filtrationfiltered through a pad of a mixture of celite and florisil
8. customPurification by flash chromotography (silica gel, hexane/ethyl acetate, 4:1)

ORD record

ord-261222eb6d5f4122b23c831fe8a56690

Source dataset

uspto-grants-1997_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05652235