Hydrogen Peroxide → HCID 123453204, compound

HRID 1854568Notes

Reaction equation

HRID 1854568 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:20]=[CH2:21])[C@H:12]([CH3:22])[N:11]1[C:23](=[O:33])[CH2:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH-:34].[Na+].OO>C1COCC1>[Si:1]([O:8][CH2:9][C@H:10]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][C:17]=2[CH:20]([OH:34])[CH3:21])[C@H:12]([CH3:22])[N:11]1[C:23](=[O:33])[CH2:24][C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 123662034HCID 123662034, compound

Product 1

HCID 123453204HCID 123453204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Dissolve 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-1-methyl-5-vinyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (477 mg, 0.95 mmol) in THF (9.5 mL). Cool to 0° C. Add BH3 (1.9 mL, 1.89 mmol, 1M in THF). Stir 4 h at room temperature. Cool to 0° C. Add NaOH (3.8 mL, 3 M in water) and H2O2 (0.58 mL, 30% wt/wt % in water). Stir overnight at room temperature. Add ethyl acetate, wash with saturated NaHCO3 solution and brine, dry over sodium sulfate, filter, and concentrate under reduced pressure to give a residue. Purify the residue by silica gel chromatography, eluting with ethyl acetate: hexanes (gradient, 5-60%) to give 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(1-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one (mixture of diastereomers) as a white foam (92 mg, 0.19 mmol). MS (m/z): 522 (M+1); and 1-((1S,3R)-3-(((tert-butyldimethylsilyl)oxy)methyl)-5-(2-hydroxyethyl)-1-methyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-(2,6-dichlorophenyl)ethan-1-one as a white foam (254 mg, 0.49 mmol). MS (m/z): 522 (M+1).

Workup

  1. additionAdd
  2. temperatureCool to 0° C
  3. stirringStir overnight at room temperature
  4. washAdd ethyl acetate, wash with saturated NaHCO3 solution and brine
  5. dry with materialdry over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customto give a residue
  9. customPurify the residue by silica gel chromatography
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-d1ce472d899a4fa5b5e6d93493c5370a
Source dataset
uspto-grants-2015_02
Patent number
US08962654B2

Reaction notes

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