Boron trifluoride etherate → HCID 59756821, compound

HRID 1665811Notes

Reaction equation

HRID 1665811 reaction equation
C(O[CH:5]1[C:21]2=[N:22][CH:23]=[CH:24][CH:25]=[C:20]2[C:7]2([CH2:12][CH2:11][N:10]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:9][CH2:8]2)[O:6]1)(=O)C.C([SiH](CC)CC)C.B(F)(F)F.CCOCC>ClCCl>[CH2:13]([N:10]1[CH2:11][CH2:12][C:7]2([C:20]3[C:21](=[N:22][CH:23]=[CH:24][CH:25]=3)[CH2:5][O:6]2)[CH2:8][CH2:9]1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 12052TriethylsilaneHCID 59756814HCID 59756814, compound

Product 1

HCID 59756821HCID 59756821, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.80 g (2.4 mmol) 1′-benzyl-7H-spiro[furo[3,4-b]pyridine-5,4′-piperidin]-7-yl acetate in 47 ml dichloromethane were subsequently added 2.8 ml (18 mmol) triethylsilane and 2.2 ml (18 mmol) boron trifluoride etherate at room temperature. The reaction mixture was heated at reflux over night. The cooling bath was then removed and the reaction mixture was diluted with dichloromethane. The organic layer was washed with aqueous 2 M sodium hydroxide solution. The aqueous layer was extracted with two portions of dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Flash-chromatography (aminopropyl-modified silica gel) gave the title compound (0.59 g, 89%) as a colorless oil.

Workup

  1. customat room temperature
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux over night
  4. customThe cooling bath was then removed
  5. additionthe reaction mixture was diluted with dichloromethane
  6. washThe organic layer was washed with aqueous 2 M sodium hydroxide solution
  7. extractionThe aqueous layer was extracted with two portions of dichloromethane
  8. dry with materialThe combined organic layers were dried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d1686ad266e24e0a8cfc2a48f6a47005
Source dataset
uspto-grants-2011_10
Patent number
US08039624B2

Reaction notes

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