Hydrogen Peroxide → HCID 59226061, compound

HRID 2370281Notes

Reaction equation

HRID 2370281 reaction equation
B1C2CCCC1CCC2.[C:10]([O:14][C:15](=[O:46])[NH:16][C:17]1([CH2:43][CH:44]=[CH2:45])[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][C:33]=2[Cl:34])[C:30]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:29][CH:28]=[CH:27]3)[CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11].[OH-:47].[Na+].OO>C1COCC1>[C:10]([O:14][C:15](=[O:46])[NH:16][C:17]1([CH2:43][CH2:44][CH2:45][OH:47])[CH2:22][CH2:21][CH:20]([O:23][C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][C:33]=2[Cl:34])[C:30]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:29][CH:28]=[CH:27]3)[CH2:19][CH2:18]1)([CH3:13])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 59226059HCID 59226059, compound

Product 1

HCID 59226061HCID 59226061, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.87 mL (1.43 mmol) of a 0.5M solution of 9-BBN in THF were added to a solution of 250 mg (0.48 mmol) of [1-allyl-4-(1-benzyloxy-7-chloro-isoquinolin-6-yloxy)-cyclohexyl]-carbamic acid tert-butyl ester (52) in 5 mL THF at 0° C. The reaction mixture was allowed to warm to room temperature over night, before being cooled to 0° C. Then, 5 mL of 3M aqueous sodium hydroxide and 5 mL of 30% aqueous hydrogen peroxide were added slowly, and the mixture was stirred for 5 h. The mixture was extracted twice with ethyl acetate, washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated in vacuo. 196 mg of the title compound 53 could be isolated as mixture of diastereoisomers in a purity sufficient for further conversion. Rt=2.05 min (Method C). Detected mass: 541.3 (M+H+).

Workup

  1. temperaturebefore being cooled to 0° C
  2. extractionThe mixture was extracted twice with ethyl acetate
  3. washwashed with water and saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aac3f9abff2a4f939cf531e3f896c2b0
Source dataset
uspto-grants-2014_04
Patent number
US08710077B2

Reaction notes

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