Cyclohexanone → HCID 178420523, compound

HRID 731490Notes

Reaction equation

HRID 731490 reaction equation
[O:1]([C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CC([O-])=O.[Na+].C([BH3-])#N.[Na+]>C1COCC1.CO>[CH:15]1([NH:14][C@H:11]2[CH2:10][CH2:9][C@H:8]([O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 4

HCID 7967CyclohexanoneHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 178511703HCID 178511703, compound

Product 1

HCID 178420523HCID 178420523, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of trans-4-phenoxycyclohexylamine (1 mmol) in 6 ml of THF and 6 ml of MeOH was added cyclohexanone (2 mmol), NaOAc (2 mmol) and 3 g of 3 Å molecular sieves. The mixture is stirred for 10 min after which 1N sodiumcyanoborohydride in tetrahydrofuran (2.4 mmol) is added. The reaction is stirred 1 day 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 crude cyclohexyl-(trans-4-phenoxy-cyclohexyl)amine which was used in the next step without further purification.

Workup

  1. additionis added
  2. filtrationthen filtered through celite
  3. washwashing through with 30 mL of dichloromethane
  4. washThe organic phase is washed with 10 ml of water, 10 mL of brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-538ac8b7bd87498d9e9dddf310ad02f8
Source dataset
uspto-grants-2009_09
Patent number
US07582769B2

Reaction notes

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