Isoamyl Nitrite → HCID 86676259, compound

HRID 1045787Notes

Reaction equation

HRID 1045787 reaction equation
CC([O-])(C)C.[K+].[Si:7]([O:14][CH2:15][CH2:16][N:17]1[C:23]2[N:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]2[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=2[CH2:19][C:18]1=[O:32])([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[N:33](OCCC(C)C)=[O:34]>O1CCCC1>[Si:7]([O:14][CH2:15][CH2:16][N:17]1[C:23]2[N:24]=[CH:25][CH:26]=[CH:27][C:22]=2[C:21]2[CH:28]=[CH:29][CH:30]=[CH:31][C:20]=2[C:19](=[N:33][OH:34])[C:18]1=[O:32])([C:10]([CH3:13])([CH3:11])[CH3:12])([CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 8053Isoamyl NitriteHCID 23665647Potassium tert-butoxideHCID 712371035-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]-5,7-dihydro-6H-pyrido[3,2-a][3]benzazepin-6-one

Product 1

HCID 86676259HCID 86676259, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add potassium 2-methylpropan-2-olate (66.1 g, 588.8 mmol) to a solution of 5-[2-(tert-butyl(dimethyl)silyl)oxyethyl]-7H-pyrido[2,3-d][3]benzazepin-6-one (155.0 g, 420.6 mmol) in tetrahydrofuran (1.6 L) at −5° C. and stir for 10 minutes. Add isoamyl nitrite (61.9 mL, 462.6 mmol) dropwise at −5° C. and stir mixture for 10 minutes. Pour over ice/water (2 L) and extract with ethyl acetate (3×200 mL). Wash combined organics with brine (200 mL), dry over sodium sulfate. Add toluene (1 L) and concentrate (×3) to obtain the title compound as a thick brown oil (160.0 g, 402.5 mmol, 96%). MS (m/z): 398 (M+1).

Workup

  1. extractionextract with ethyl acetate (3×200 mL)
  2. washWash
  3. dry with materialdry over sodium sulfate
  4. concentrationAdd toluene (1 L) and concentrate (×3)

Sources & evidence

ORD record
ord-d110f445a2d94912937f960645e111b1
Source dataset
uspto-grants-2013_10
Patent number
US08569286B2

Reaction notes

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