Water → 6,7-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2,3,4-tetrahydroisoquinoline

HRID 863893Notes

Reaction equation

HRID 863893 reaction equation
Br.[CH2:2]1[C:11]2[C:6](=[CH:7][C:8]([OH:13])=[C:9]([OH:12])[CH:10]=2)[CH2:5][CH2:4][NH:3]1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].O>N1C=CC=CC=1>[CH3:18][C:17]([Si:14]([CH3:16])([CH3:15])[O:13][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][C:9]=1[O:12][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:2][NH:3][CH2:4][CH2:5]2)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 27244601,2,3,4-Tetrahydro-6,7-isoquinolinediol hydrobromide

Product 1

HCID 190421026,7-Bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1,2,3,4-tetrahydroisoquinolineYield 100%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.0 g of 1,2,3,4-tetrahydro-6,7-isoquinolinediol hydrobromide and 2.45 g of t-butyl dimethylsilyl chloride in 25.0 mL of pyridine is heated under reflux for 4.5 hours, cooled, poured into water and extracted with diethyl ether. The diethyl ether extract is washed with brine, dried, filtered. The filtrate is evaporated to yield a brown oil. This oil is purified by Kugelrohr distillation to yield 1.6 g of the desired product as a yellow solid, b.p. 155° C., 350 torr.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 4.5 hours
  3. temperaturecooled
  4. extractionextracted with diethyl ether
  5. extractionThe diethyl ether extract
  6. washis washed with brine
  7. customdried
  8. filtrationfiltered
  9. customThe filtrate is evaporated
  10. customto yield a brown oil
  11. distillationThis oil is purified by Kugelrohr distillation

Sources & evidence

ORD record
ord-fe041f5da31f4a35b5e8f49c4a01d795
Source dataset
uspto-grants-1996_10
Patent number
US05561141

Reaction notes

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