Pyridine → 7-[[(1,1-Dimethylethyl)dimethylsily]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

HRID 863878

反応式

HRID 863878 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[CH2:8][NH:7][CH2:6][CH2:5]2.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CC=C[CH:23]=1>>[CH3:18][C:17]([Si:14]([CH3:16])([CH3:15])[O:12][C:11]1[CH:10]=[C:9]2[C:4]([CH2:5][CH2:6][NH:7][CH2:8]2)=[CH:3][C:2]=1[O:1][CH3:23])([CH3:20])[CH3:19]

参加物

4

反応物 3

HCID 1049PyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 4172897-Methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol

生成物 1

HCID 152855547-[[(1,1-Dimethylethyl)dimethylsily]oxy]-1,2,3,4-tetrahydro-6-methoxyisoquinoline

実験手順

To a solution of 19.2 g of 6-hydroxy-7-methoxy-1,2,3,4-tetrahydroisoquinoline in 425 mL of pyridine is added 48.4 g of t-butyl-dimethylsilylchloride and 0.5 g of 4-N,N-dimethylaminopyridine. The solution is heated to reflux for 3.5 hours and the volatiles removed at 70° C. by distillation. The residue is partitioned between aqueous potassium bicarbonate and ethyl acetate. The organic layer is washed with water, dried (magnesium sulfate) and the volatiles removed in vacuo. The residue is suspended in diethyl ether, filtered and washed with hexane. The filtrate is evaporated and the residue distilled via Kugelrohr at 150 mm and 120°-130° C. to afford 26.2 g of the desired product as a colorless oil. MS(CI): m/z 294(MH+). Calcd for C16H27NO2Si 1/4H2O: C=64.49, H=9.31, N=4.70, Si=9.43 Found C=64.46, H=9.03, N=4.70, Si=9.52

後処理

  1. temperatureThe solution is heated
  2. temperatureto reflux for 3.5 hours
  3. customthe volatiles removed at 70° C. by distillation
  4. customThe residue is partitioned between aqueous potassium bicarbonate and ethyl acetate
  5. washThe organic layer is washed with water
  6. dry with materialdried (magnesium sulfate)
  7. customthe volatiles removed in vacuo
  8. filtrationfiltered
  9. washwashed with hexane
  10. customThe filtrate is evaporated
  11. distillationthe residue distilled via Kugelrohr at 150 mm and 120°-130° C.

出典と根拠

ORDレコード
ord-15caa5acb864454d84165c4114623937
出典データセット
uspto-grants-1996_10
特許番号
US05561141

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