Tetrahydrofuran → 1'-(t-butyloxycarbonyl)-3,4-dihydro-3-oxospiro[1H-indene-1,4'-piperidine]

HRID 1735466Notes

Reaction equation

HRID 1735466 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].C1C[O:25]CC1.B1C2CCCC1CCC2.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>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:25])[CH2:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 789669-Borabicyclo(3.3.1)nonaneHCID 3653579Tert-butyl Spiro[indene-1,4'-piperidine]-1'-carboxylateHCID 178418287HCID 178418287, compound

Product 1

HCID 190304391'-(t-butyloxycarbonyl)-3,4-dihydro-3-oxospiro[1H-indene-1,4'-piperidine]Yield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 (1.0 M 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

  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 chromotgraphy (silica gel, hexane/ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-975fdd66e3394d4489fe7553dc8fac2e
Source dataset
uspto-grants-1996_07
Patent number
US05536716

Reaction notes

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