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

HRID 1902146Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B1C2CCCC1CCC2.C1C=C[NH+]=CC=1.[O-:37][Cr](Cl)(=O)=O>C1COCC1.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([C:21]3[CH:16]([CH2:17][CH:18]=[CH:19][CH:20]=3)[C:15](=[O:37])[CH2:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 70 °C

Procedure

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 chromotgraphy (silica gel, hexane/ethyl acetate, 4:1) gave 326 mg (47%) of the title compound.

Workup

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

Sources & evidence

ORD record: ord-2f8bf92067a5443dbe8b4766367e397f
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05578593

Reaction notes

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