Hydrochloric Acid → HCID 11681854, compound

HRID 2247314Notes

Reaction equation

HRID 2247314 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]([CH3:23])([CH3:22])[C:13]([NH:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:14])=[CH:7][CH:6]=1)[CH:2]=[CH2:3].B1C2CCCC1CCC2.[OH-:33].[Na+].OO.Cl>C1COCC1.C(Cl)Cl.O.C(O)C>[CH:16]1([NH:15][C:13](=[O:14])[C:12]([S:11][C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:1][CH2:2][CH2:3][OH:33])=[CH:10][CH:9]=2)([CH3:23])[CH3:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 11667135HCID 11667135, compound

Product 1

HCID 11681854HCID 11681854, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-(Allyloxy)phenyl]thio}-N-cyclohexyl-2-methylpropanamide was dissolved in THF and treated with 9-BBN at rt under N2. After stirring at rt for 18 h, ethanol, 1N NaOH and a 30% H2O2 solution were added successively to the reaction mixture. After stirring for a few hours, the reaction mixture was acidified with 1N HCl to pH 2. Water and CH2Cl2 were added and the layers were separated. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (silica, hexanes:EtOAc, 2:1 to 1:1) to provide the desired alcohol as a white solid. LCMS: (M+H)+=352.2.

Workup

  1. stirringAfter stirring for a few hours
  2. customthe layers were separated
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography (silica, hexanes:EtOAc, 2:1 to 1:1)

Sources & evidence

ORD record
ord-65e019d3c9744062a0a453f33294a124
Source dataset
uspto-grants-2010_03
Patent number
US07687665B2

Reaction notes

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