Cyclohexanone → HCID 86634385, compound

HRID 1191285Notes

Reaction equation

HRID 1191285 reaction equation
[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][NH:17][CH:16]3[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:31]1(=O)[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.CN(C)C=O>[N:1]1([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]3[CH2:20][CH2:19][CH2:18][N:17]([CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)[CH:16]3[CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])[N:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

8

Reactant 5

HCID 7967CyclohexanoneHCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 86634384HCID 86634384, compound

Product 1

HCID 86634385HCID 86634385, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The compound 20 (151 mg), dimethylformamide (3 mL), acetic acid (0.03 mL), cyclohexanone (0.37 mL), anhydrous sodium sulfate (800 mg) and sodium triacetoxyborohydride (765 mg) were stirred at room temperature for 1 day. The reaction solution was added aqueous 2N sodium hydroxide solution and extracted with dichloromethane. The extract was dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=80:10:1) to obtain the title compound (118 mg) having the following physical properties.

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol:triethylamine=80:10:1)

Sources & evidence

ORD record
ord-a11a8e4c0cc3436fa1e80d7936e99a85
Source dataset
uspto-grants-2014_03
Patent number
US08680092B2

Reaction notes

Loading…