HCID 123708140, compound → HCID 123347188, compound

HRID 1854577Notes

Reaction equation

HRID 1854577 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:5]=1[CH2:6][C@H:7]([CH2:26][O:27][Si:28]([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29])[N:8]([C:15](=[O:25])[CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])[C@H:9]2[CH3:14])(=[O:3])[CH3:2].[CH3:35][Mg]Cl>C1COCC1>[Si:28]([O:27][CH2:26][C@H:7]1[CH2:6][C:5]2[C:10](=[CH:11][CH:12]=[CH:13][C:4]=2[C:1]([OH:3])([CH3:35])[CH3:2])[C@H:9]([CH3:14])[N:8]1[C:15](=[O:25])[CH2:16][C:17]1[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=1[Cl:24])([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:30])[CH3:29]

Participants

4

Reactant 2

HCID 123708140HCID 123708140, compoundHCID 178418332HCID 178418332, compound2×

Product 1

HCID 123347188HCID 123347188, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 1-((1S,3R)-5-acetyl-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (68 mg, 130 μmol) in THF (1.3 mL). Cool to 0° C., add MeMgCl (87 μL, 261 μmol, 3M in Et2O). Stir 30 min at 0° C. and 30 min at room temperature. Add MeMgCl (87 μL, 261 μmol, 3M in Et2O) at rt. Stir 60 min. Add water and extract with ethyl acetate three times. Combine the ethyl acetate extracts, dry over sodium sulfate, filter, and concentrate under reduced pressure to give the title compound as a white foam (0.054 g, 100 μmol). MS (m/z): 536.2 (M+1).

Workup

  1. customat rt
  2. stirringStir 60 min
  3. extractionAdd water and extract with ethyl acetate three times
  4. dry with materialdry over sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-4fcd91919299444fa7c13f4fe66999a0
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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