Hydrogen Peroxide → HCID 67268348, compound

HRID 252454Notes

Reaction equation

HRID 252454 reaction equation
[CH:1]1([C@@H:7]([C:11]2[C:12]([NH2:28])=[N:13][C:14]3[C:19]([CH:20]=2)=[CH:18][C:17]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:16][CH:15]=3)[CH2:8][CH:9]=[CH2:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B1C2CCCC1CCC2.[OH-:38].[Na+].OO>O1CCCC1.O>[NH2:28][C:12]1[C:11]([C@H:7]([CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH2:8][CH2:9][CH2:10][OH:38])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:18]=2)[N:13]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 57475714HCID 57475714, compound

Product 1

HCID 67268348HCID 67268348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((S)-1-cyclohexyl-but-3-enyl)-6-phenoxy-quinolin-2-ylamine (0.82 g, 2.2 mmol) in tetrahydrofuran (5.5 mL) at −20° C. was added 9-BBN (0.5 M in THF, 17.6 mL, 8.8 mol) dropwise over 20 min. The reaction mixture was stirred overnight while it reached room temperature. To the reaction mixture at 0° C. was then added aqueous 1N NaOH solution (8.2 mL) and aqueous 30% H2O2 solution (8.2 mL) and stirring was continued for 2.0 h. Water (15.0 mL) was added to the reaction mixture which was then extracted with EtOAc. The separated organic layer was dried (MgSO4) and concentrated in vacuo to yield crude material. The crude material was purified by silica gel column chromatography using 10% MeOH in CHCl3 to yield 4-(2-amino-6-phenoxy-quinoline-3-yl)-4-(S)-cyclohexyl-butan-1-ol.

Workup

  1. customreached room temperature
  2. customat 0° C.
  3. waitwas continued for 2.0 h
  4. extractionwas then extracted with EtOAc
  5. dry with materialThe separated organic layer was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto yield crude material
  8. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-02892ff1ca414d37a234a506f935dd66
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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