(2-Bromoethoxy)-tert-butyldimethylsilane → HCID 22597805, compound

HRID 1760235Notes

Reaction equation

HRID 1760235 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].Br[CH2:15][CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:17][CH2:16][CH2:15][N:10]1[CH2:9][CH2:8][C:7]2[C:12](=[CH:13][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)[CH2:11]1)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 64248331,2,3,4-Tetrahydro-7-nitroisoquinoline

Product 1

HCID 22597805HCID 22597805, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-Nitro-tetrahydroisoquinoline (5.0 g; 28.0 mmol) was dissolved in DMF (150 ml). This solution was treated with (2-bromoethoxy)-tert-butyl-dimethylsilane (12.0 ml; 56.0 mmol), and stirred at 80° C. overnight. The mixture was cooled to room temperature and the solvent removed in vacuo. Purification by column chromatography through SiO2, eluting with 50% diethyl ether/petroleum ether gave the title compound (4.2 g, 44%).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe solvent removed in vacuo
  3. customPurification by column chromatography through SiO2
  4. washeluting with 50% diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-de87bb48f0974181bd9c3ed3d08ceed7
Source dataset
uspto-grants-2005_01
Patent number
US06841560B2

Reaction notes

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