Hydrogen Peroxide → HCID 66685206, compound

HRID 579204Notes

Reaction equation

HRID 579204 reaction equation
C[O:2][C:3]([C:5]1[S:6][C:7]([C:26]#[C:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:8][C:9]=1[N:10]1[CH:15]([CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH2:14][CH2:13][C@@H:12]([CH2:22][CH:23]=[CH2:24])[C:11]1=[O:25])=[O:4].B1C2CCCC1CCC2.[OH-:41].[Na+].OO>C1COCC1.CCO>[CH:16]1([CH:15]2[N:10]([C:9]3[CH:8]=[C:7]([C:26]#[C:27][C:28]([CH3:30])([CH3:31])[CH3:29])[S:6][C:5]=3[C:3]([OH:2])=[O:4])[C:11](=[O:25])[C@H:12]([CH2:22][CH2:23][CH2:24][OH:41])[CH2:13][CH2:14]2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonaneHCID 666846113-((S)-3-Allyl-6-cyclohexyl-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 66685206HCID 66685206, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-((S)-3-allyl-6-cyclohexyl-2-oxo-piperidin-1-yl)-5-(3,3-dimethyl-but-1-ynyl)-thiophene-2-carboxylic acid methyl ester (less polar diastereomer from previous step) (60 mg, 0.14 mmol, 1.0 equiv) in anhydrous THF (2.0 ml) was added 9-BBN (0.5 M in THF, 0.68 ml, 0.34 mmol, 2.5 equiv) at 0° C. and the resulting solution was stirred at room temperature for 2 hours. The solution was then cooled at 0° C. and to the solution was added EtOH, 1.0 M aq. NaOH solution and aqueous H2O2 solution. The reaction mixture was heated to reflux for 90 minutes and then cooled at room temperature. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated under vacuum. The residue was purified by prep-HPLC (0.1% NH4OH) to give 20 mg of the desired product (yield 33%). MS: 446 [M+H+]. 1H-NMR (400 MHZ, CD3OD): 6.81 (s, 1H), 4.00 (br, 1H), 3.53 (t, 2H), 2.27 (br, 1H), 1.97 (m, 3H), 1.82˜1.64 (m, 7H), 1.58 (m, 2H), 1.37 (m, 2H), 1.31 (s, 9H), 1.14 (m, 5H).

Workup

  1. temperatureThe solution was then cooled at 0° C. and to the solution
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux for 90 minutes
  4. temperaturecooled at room temperature
  5. extractionThe mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified by prep-HPLC (0.1% NH4OH)

Sources & evidence

ORD record
ord-7ac886c577ca4bc4a0569b32592d2bea
Source dataset
uspto-grants-2015_05
Patent number
US09040690B2

Reaction notes

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