Cyclohexanone → HCID 10550601, compound

HRID 971057Notes

Reaction equation

HRID 971057 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[C:27]1(=O)[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.[BH4-].[Na+].N.O>C(O)C>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[C:12]2[CH2:13][CH2:14][N:15]([CH:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:16][CH2:17]2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:9][CH:10]=1)[CH3:26]

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 4311764Sodium borohydrideHCID 9841259ARM390HCID 12896473Azane;hydrate

Product 1

HCID 10550601HCID 10550601, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of compound 6 (100 mg, 0.29 mmol), cyclohexanone (36 ul, 0.35 mmol) and Ti(OPr-i)4 (0.17 ml, 0.58 mmol) was ultrasonicated for 1 hr and then stirred at rt overnight under a nitrogen atmosphere. The mixture was diluted with ethanol (5 ml) and followed by addition of NaBH4 (33 mg, 0.87 mmol). The resulting mixture was stirred for 12 hr at rt. 2N NH3.H2O was added to quench the reaction and the mixture filtered through celite. The filtrate was extracted with ethyl acetate several times and the combined organic phases washed with water and brine, and dried over Na2SO4. Concentration in vacuo and MPLC purification (0:100 to 100:0 EtOAc:Heptane eluting on silcal gel 60) gave the title compound (24 mg, 20%).

Workup

  1. customwas ultrasonicated for 1 hr
  2. stirringThe resulting mixture was stirred for 12 hr at rt
  3. customto quench
  4. customthe reaction
  5. filtrationthe mixture filtered through celite
  6. extractionThe filtrate was extracted with ethyl acetate several times
  7. washthe combined organic phases washed with water and brine
  8. dry with materialdried over Na2SO4
  9. concentrationConcentration
  10. customin vacuo and MPLC purification (0:100 to 100:0 EtOAc:Heptane eluting on silcal gel 60)

Sources & evidence

ORD record
ord-7df9e689cd4947e6b9ada14d726fb776
Source dataset
uspto-grants-2007_12
Patent number
US07312336B2

Reaction notes

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