Acetone → HCID 69285620, compound

HRID 2225300Notes

Reaction equation

HRID 2225300 reaction equation
[NH2:1][C@H:2]1[CH2:7][C@@H:6]([CH2:8][C:9]#[N:10])[C@@H:5]([N:11]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C=O.C([O-])([O-])=O.[Na+].[Na+].[CH3:48][C:49]([CH3:51])=O>ClC(Cl)C>[CH2:19]([N:11]([CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C@H:5]1[CH2:4][CH2:3][C@@H:2]([N:1]([CH:49]([CH3:51])[CH3:48])[CH3:26])[CH2:7][C@H:6]1[CH2:8][C:9]#[N:10])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 5

HCID 180AcetoneHCID 712FormaldehydeHCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydride2×HCID 69286687HCID 69286687, compound

Product 1

HCID 69285620HCID 69285620, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Examples 11p and 11q, Step 6: To a solution of 2-((1S,2S,5R)-5-amino-2-(dibenzylamino)cyclohexyl)acetonitrile (4.35 mmoles) in 40 ml of anhydrous dichloroethane was added acetone (3.5 ml), and the mixture was stirred for 30 minutes at room temperature. Then sodium triacetoxyborohydride (3 g) was added, and the mixture was stirred for 1.5 hours. To the mixture was added 37% aqueous formaldehyde (2.2 ml) and it was stirred for 15 minutes. Then additional 1.6 g of sodium triacetoxyborohydride was added, and the mixture was continued to stir for 2.5 hours. At the end of the stirring, was added saturated Na2CO3, and the product was extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated to give an oily residue. It was purified by column chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2) to give 1 g of ((1S,2S,5R)-2-(dibenzylamino)-5-(isopropyl(methyl)amino)cyclohexyl)acetonitrile as an oil.

Workup

  1. stirringthe mixture was stirred for 1.5 hours
  2. stirringwas stirred for 15 minutes
  3. stirringto stir for 2.5 hours
  4. extractionthe product was extracted with EtOAc
  5. washThe extract was washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated
  8. customto give an oily residue
  9. customIt was purified by column chromatography (silica gel, 0.5:4.5:95 cNH4OH-MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-c207b08738f74f82bf6067bcf7e09b7f
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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