Dichloromethane → HCID 178482720, compound

HRID 722032Notes

Reaction equation

HRID 722032 reaction equation
C(Cl)Cl.[C:4]([O:8][C:9]([NH:11][CH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1)=[O:10])([CH3:7])([CH3:6])[CH3:5].[CH3:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+]>[CH2:21]([N:20]([CH3:19])[C@H:15]1[CH2:16][CH2:17][C@H:12]([NH:11][C:9]([O:8][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:10])[CH2:13][CH2:14]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 7669N-MethylbenzylamineHCID 1512535tert-butyl N-(4-oxocyclohexyl)carbamateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 178482720HCID 178482720, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To 160 ml of a methylene chloride solution containing 16.93 g of 4-(tert-butoxycarbonylamino)cyclohexanone and 10.55 ml of N-methylbenzylamine was added 19.08 g of sodium triacetoxyborohydride under ice-cooling, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was diluted with an aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The obtained residue was suspended in hexane and collected by filtration. This mother liquor was concentrated and the residue was purified by NH-silica gel chromatography (solvent: hexane-ethyl acetate (97:3 to 83:17)). The residue was further suspended in hexane and collected by filtration and combined with the filtered product to obtain 13.55 g of N′-benzyl-N-tert-butoxycarbonyl-N′-methyl-trans-1,4-cyclohexanediamine.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationcollected by filtration
  7. concentrationThis mother liquor was concentrated
  8. customthe residue was purified by NH-silica gel chromatography (solvent: hexane-ethyl acetate (97:3 to 83:17))
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-634c67c9667e4552bfd4b29135ba546f
Source dataset
uspto-grants-2006_11
Patent number
US07138397B2

Reaction notes

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