Water → (R)-5-Bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydroisoquinoline

HRID 1854552Notes

Reaction equation

HRID 1854552 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C@H:5]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[NH:6][CH2:7]2.ClN1C(=O)CCC1=O.[OH-].[K+].O>C(OCC)C>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][C@H:5]([CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:15])[CH3:16])[N:6]=[CH:7]2

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 31398ChlorosuccinimideHCID 123224990[(3R)-5-Bromo-1,2,3,4-tetrahydroisoquinolin-3-YL]methoxy-tert-butyl-dimethyl-silane

Product 1

HCID 123546513(R)-5-Bromo-3-(((tert-butyldimethylsilyl)oxy)methyl)-3,4-dihydroisoquinolineYield 81.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Dissolve (3R)-5-bromo-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-1,2,3,4-tetrahydroisoquinoline (4.2 g, 11.8 mmol) in diethyl ether (118 mL). Add N-chlorosuccinimide (2.36 g, 17.7 mmol). Stir 30 min at room temperature and concentrate under reduced pressure. Dissolve the residue in potassium hydroxide (42.0 mL, 30.3 mmol, 5% in MeOH) and stir for 30 min at room temperature. Pour into water and extract with dichloromethane. Dry the dichloromethane extracts over sodium sulfate, filter, and concentrate under reduced pressure. Purify the residue by silica gel chromatography eluting with ethyl acetate: hexanes (5-100% gradient) to give the title compound (3.40 g, 9.59 mmol). MS (m/z): 354 (M+1).

Workup

  1. concentrationconcentrate under reduced pressure
  2. stirringstir for 30 min at room temperature
  3. extractionextract with dichloromethane
  4. dry with materialDry the dichloromethane
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure
  7. customPurify the residue by silica gel chromatography
  8. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-1a60ff61d4824fe682f29b05eca8e3ad
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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