Cyclohexanone → HCID 178420520, compound

HRID 731465Notes

Reaction equation

HRID 731465 reaction equation
FC(F)(F)C(O)=O.[O:8]([CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([NH2:22])[CH2:18][CH2:17]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:23]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.C([BH3-])#N.[Na+]>C1COCC1.CO>[CH:23]1([NH:22][C@H:19]2[CH2:20][CH2:21][C@H:16]([CH2:15][O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:17][CH2:18]2)[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 178511557HCID 178511557, compound

Product 1

HCID 178420520HCID 178420520, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Trans-4-phenoxymethylcyclohexylamine trifluoroacetate (1.2 mmol) is dissolved in a mixture of 4 ml of THF and 4 mL of MeOH in a 20 ml glass vial equipped with a magnetic stirrer and a screw cap. 117 mg of cyclohexanone and 3 g of 3 Å molecular sieves are added. The mixture is stirred for 10 min. after which 2.4 mL of 1N sodiumcyanoborohydride in tetrahydrofuran is added. The reaction stirred 4 days at room temperature then filtered through celite washing through with 30 mL of dichloromethane. The organic phase is washed with 10 mL of water, 10 mL of brine, dried (MgSO4), filtered and concentrated in vacuo to give 300 mg of cyclohexyl-(trans-4-phenoxymethyl-cyclohexyl)-amine.

Workup

  1. customequipped with a magnetic stirrer
  2. customa screw cap
  3. additionis added
  4. filtrationthen filtered through celite
  5. washwashing through with 30 mL of dichloromethane
  6. washThe organic phase is washed with 10 mL of water, 10 mL of brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-73de901e6a394524869af492cd8e1c84
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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